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Catalytic Asymmetric Reactions
of Conjugated Nitroalkenes
Taylor & Francis
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Catalytic Asymmetric Reactions
of Conjugated Nitroalkenes

Irishi N. N. Namboothiri, Meeta Bhati, Madhu Ganesh,

Basavaprabhu Hosamani, Thekke V. Baiju, Shimi Manchery,
and Kalisankar Bera
First edition published 2020
by CRC Press
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and by CRC Press

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Typeset in Times
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Dedicated to Professor Alfred Hassner on the occasion of his 90th birthday
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Contents
List of Abbreviations......................................................................................................................... xi
Foreword......................................................................................................................................... xiii
Preface.............................................................................................................................................. xv
Authors ...........................................................................................................................................xvii

Introduction....................................................................................................................................... 1

Chapter 1 Catalytic Asymmetric Michael Addition of 1,3-Dicarbonyls to Nitroalkenes ............ 7

1.1 Introduction ....................................................................................................... 7
1.2 Addition of 1,3-Diketones ................................................................................. 7
1.3 Addition of Malonates...................................................................................... 14
1.4 Addition
 of β-Ketoesters ................................................................................. 26
1.5 Addition of 2-Hydroxynaphthoquinones ......................................................... 33
1.6 Addition of Hydroxycoumarin ........................................................................ 35
1.7 Addition of Meldrum’s Acid............................................................................. 37
1.8 Conclusions...................................................................................................... 39
References .................................................................................................................. 39

Chapter 2 Catalytic Asymmetric Michael Addition of Aldehydes to Nitroalkenes ................... 43

2.1 Introduction ..................................................................................................... 43
2.2 Addition of Aldehyde Enolates........................................................................ 43
2.3 Addition of Umpolung of Aldehydes: The Stetter Reaction............................ 71
2.4 Conclusions...................................................................................................... 73
References................................................................................................................... 73

Chapter 3 Catalytic Asymmetric Michael Addition of Ketones to Nitroalkenes........................ 77

3.1 Introduction
 ..................................................................................................... 77
3.2 Addition of Aliphatic and Aromatic Ketones................................................... 77
3.3 Addition
 of α-Ketoesters, α-Ketoamides and α-Ketophosphonates............... 107
3.4 Addition of β-Ketosulfones ........................................................................... 111
3.5 Conclusions
 ..................................................................................................... 112
References ................................................................................................................ 112

Chapter 4 Catalytic Asymmetric Michael Addition of Miscellaneous Carbonyl

Compounds to Nitroalkenes ..................................................................................... 115
4.1 Introduction
 .................................................................................................... 115
4.2 Addition of Esters/Lactones: Iminoesters, Furanones,
Oxazolones and Isoxazolones������������������������������������������������������������������������ 115
4.3 Addition of Amides/Lactams: Oxindoles, Pyrazolones and Pyrrolidones ... 122
4.4 Conclusions.................................................................................................... 134
References ................................................................................................................ 134

vii
viii Contents

Chapter 5 Catalytic Asymmetric Friedel–Crafts Reactions of Nitroalkenes............................ 137

5.1 Introduction
 ................................................................................................... 137
5.2 Friedel–Crafts Reaction ................................................................................ 137
5.3 Conclusions.................................................................................................... 158
References ................................................................................................................ 158

Chapter 6 Catalytic Asymmetric Michael Addition of Miscellaneous Carbon-centered

Nucleophiles to Nitroalkenes ................................................................................... 161
6.1 Introduction ................................................................................................... 161
6.2 Addition of Nitroalkanes................................................................................ 161
6.3 Addition of Cyanides...................................................................................... 166
6.4 Addition of Boronic Acids.............................................................................. 168
6.5 Addition of Malononitrile............................................................................... 172
6.6 Addition of Organo-Zinc Reagents ............................................................... 174
6.7 Conclusions
 .................................................................................................... 180
References ................................................................................................................ 180

Chapter 7 Catalytic Asymmetric Michael Addition of Heteroatom-centered

Nucleophiles to Nitroalkenes ................................................................................... 183
7.1 Introduction ................................................................................................... 183
7.2 Addition of Phosphorus-centered Nucleophiles ............................................ 183
7.3 Addition of Sulphur-centered Nucleophiles .................................................. 188
7.4 Addition of Nitrogen-centered Nucleophiles.................................................. 192
7.5 Addition of Oxygen-centered Nucleophiles .................................................. 195
7.6 Addition
 of Arsenic-centered Nucleophiles .................................................. 197
7.7 Conclusions
 .................................................................................................... 198
References ................................................................................................................ 198

Chapter 8 Catalytic Asymmetric Cycloadditions of Nitroalkenes ........................................... 201

8.1 Introduction ................................................................................................... 201
8.2 [3+2] Cycloadditions....................................................................................... 201
8.3 [4+2] Cycloadditions...................................................................................... 215
8.4 Other Cycloadditions...................................................................................... 221
8.5 Conclusions.................................................................................................... 223
References ................................................................................................................ 223

Chapter 9 Catalytic Asymmetric Reduction of Nitroalkenes.................................................... 227

9.1 Introduction
 .................................................................................................... 227
9.2 Metal Catalyzed Reduction............................................................................ 227
9.3 Organocatalyzed
 Reduction........................................................................... 232
9.4 Bioreduction .................................................................................................. 233
9.5 Conclusions.................................................................................................... 235
References ................................................................................................................ 235
Contents ix

Chapter 10 Catalytic Asymmetric Synthesis of Cycloalkanes via Cascade

Reactions of Nitroalkenes ........................................................................................ 237
10.1 Introduction
 .................................................................................................... 237
10.2 Synthesis of Cycloalkanes.............................................................................. 237
10.3 Conclusions..................................................................................................... 253
References ................................................................................................................ 254

Chapter 11 Catalytic Asymmetric Synthesis of Aryl-Fused Heterocycles via Cascade

Reactions of Nitroalkenes ........................................................................................ 257
11.1 Introduction
 .................................................................................................... 257
11.2 Synthesis of Aryl-Fused Heterocycles........................................................... 257
11.3 Conclusions..................................................................................................... 273
References................................................................................................................. 273

Chapter 12 Catalytic Asymmetric Synthesis of Five- and Six-Membered Heterocycles via

Cascade Reactions of Nitroalkenes .......................................................................... 275
12.1 Introduction.................................................................................................... 275
12.2 Synthesis of Five- and Six-Membered Nitrogen Heterocycles ...................... 275
12.3 Synthesis of Five- and Six-Membered Oxygen Heterocycles........................ 278
12.4 Synthesis of Spiro-Oxindoles......................................................................... 287
12.5 Conclusions.................................................................................................... 293
References ................................................................................................................ 293

Index .............................................................................................................................................. 295

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List of Abbreviations
BINAP 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl
BINOL 1,1′-Binaphthalene-2,2′-diol
BOPA Bis(oxazolinylphenyl)amide
BOX Bis-oxazoline
Cp/Rh(R)-prophos Pentamethylcyclopentadienyl rhodium (II)-
1,2-bis(diphenylphosphino)propane
Cu(CH3CN)4PF6 Tetrakis(acetonitrile)copper(I)hexafluorophosphate
Cu(OTf)2.C6H6 Benzene complex of copper(II) trifluoromethanesulfonate
Cu/Eu/Cu Trimetallic complex of copper/europium/copper
Cu/Mn Copper-manganese heterobimetals
CuOtBu Copper(I)tert-butoxide
CPME Cyclopentyl methyl ether
DABCO 1,4-Diazabicyclo[2,2,2]octane
DBAD Di-tert-butyl azodicarboxylate
DBU 1,8-Diazabicyclo[5,4,0]undec-7-ene
DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
DFT Density functional theory
DHQA Dihydroquinine
[DHQD]2PYR Hydroquinidine-2,5-diphenyl-4,6-pyrimidinediyl diether
DMA N,N-Dimethyl acetamide
DMAP 4-N,N-Dimethylaminopyridine
DMF Dimethylformamide
DMM Diaminomethylenemalononitrile
DMSO Dimethylsulfoxide
Duanphos (1R,1′R,2S,2′S)-(+)-2,2′-Di-t-butyl-2,3,2′,3′-tetrahydro-1,1′-bi-
1H-isophosphindole
DIPEA Diisopropylethylamine
ESI-MS Electrospray ionization mass spectroscopy
Fe3O4/PVP@SiO2/ProTMS (S)-Diphenylprolinol trimethylsilyl ether embedded polyvinyl-
pyrrolidone (PVP)-modified ferric oxide magnetic nanoparticle
Fe3O4@SiO2 Ferric oxide adsorbed on silica support
FOXAP 2,2″-Bis(diphenylphosphino)-1,1″-biferrocene
GABA γ-aminobutyric acid
GC Gas chromatography
HOMO Highest occupied molecular orbital
HPLC High performance liquid chromatography
HRMS High resolution mass spectrum
H-bonding Hydrogen bonding
HMPA Hexamethylphosphoramide
ILs Ionic liquids
IBX Iodoxybenzoic acid
JH-CPP Jorgensen-Hayashi chiral porous polymer
Josiphos (R)-1-[(S)-2-(Diphenylphosphino)ferrocenyl]
ethyldicyclohexylphosphine
KYE1 Enoate reductase 1 from kluyveromyces lactis
LDA Lithium diisopropylamide
LUMO Lowest unoccupied molecular orbital

xi
xii List of Abbreviations

MAO monoamine oxidase inhibitor

MBH Morita-Baylis-Hillmann
MDO Modularly designed organocatalyst
MNP Magnetic nanoparticles
MS Molecular sieves
MW Microwave
Ns Nosyl
NADH Nicotinamide adenine dinucleotide
NADPH Nicotinamide adenine dinucleotide phosphate
N-Boc tert-butyloxycarbonyl protecting group
NFSI N-Fluorobenzenesulfonimide
NHC N-Heterocyclic carbene
NHTf Trifluoromethane sulfonylamide
NMM N-Methylmorpholine
NMR Nuclear magnetic resonance
nbd 2,5-norbornadiene
OPR 12-Oxophytodienoate reductase isoenzyme
OTf trifluoromethanesulfonate
OYE Old yellow enzyme
Pd/Mn Palladium-manganese heterobimetals
Pd-Sm-Pd Trimetallic complex of palladium/samarium/palladium
PEG Polyethylene glycol
Phebim bis-(imidazolinyl)phenyl
PMHS polymethylhydrosiloxane
PMO Palladium comprising dicationic bipyridinium supported periodic
mesoporous
­ organosilica
p-tol-BINAP 2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl
PyBidine Diphenyldiamine-derived bis(imidazolidine)pyridine
PCC Pyridinium chlorochromate
PPY Polypyrrole
RT Room temperature
[Rh(nbd)2]SbF6 Bis(norbornadiene)rhodium(I)hexafluoroantimonate
(R,S)-Josiphos (R)-1-[(SP)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine
(S)-Binapine (3S,3′S,4S,4′S,11bS,11′bS)-(+)-4,4′-Di-t-butyl-4,4′,5,5′-tetrahydro-3,3′-bi-
3H-dinaphtho[2,1-c:1′,2′-e]phosphepin
selectFluor 1-Fluoro-4-methyl-1,4-diazoniabicyclo[2.2. 2]octanebis(tetrafluoroborate)
SN2’ Nucleophilic substitution unimolecular - allylic
TBDPS tert-Butyldiphenylsilyl
TEA triethylamine
TFA Trifluoroacetic acid
TMM trimethylenemethane
TMS Trimethylsilyl
TS Transition state
TsDPEN N-Tosyl-1,2-diphenyl-1,2-ethylenediamine
TBME Tert-butyl methyl ether
Foreword
As nitroalkenes are versatile compounds in terms of availability and reactivity, nitroalkenes have
been used as benchmark substrates to demonstrate the synthetic utility of catalytic reactions. In
addition, the obtained products are readily converted into important biologically active natural
products and pharmaceuticals by taking advantage of the good ability of nitro groups to be trans-
formed into various functional groups, such as hydroxylamines, amines and masked carbonyls.
Over the past few decades, the unique properties of nitroalkenes have led to a wide range of
asymmetric reactions using chiral catalysts. In 2003, we demonstrated that bifunctional amino-
thioureas efficiently promote the asymmetric Michael addition of malonates and β-ketoesters to
β-nitrostyrenes with high enantioselectivity. In the course of these studies, we recognized the syn-
thetic utility of asymmetric reactions of nitroalkenes. Later, we developed a double Michael reaction
between γ,δ-unsaturated β-ketoester and β-nitrostyrene to achieve an asymmetric total synthesis of
natural products.
To date, various types of chiral catalysts including organocatalysts and metal catalysts have
been discovered for catalytic asymmetric Michael addition and cycloaddition with nitroalkenes.
However, because of the large number of such catalysts, no one can grasp the details of all the
research results. It is, therefore, important and timely to have a comprehensive book that sum-
marizes major developments and key concepts in this booming area of asymmetric catalysis with
nitroalkenes. In this regard, Irishi Namboothiri is an appropriate author for this book as he has
published a series of papers and reviews on the application of nitroalkenes in the synthesis of carbo-
cycles and heterocycles, as well as on the Morita–Baylis–Hillman reaction of nitroalkenes.
The book contains many examples of important catalytic reactions using newly designed cata-
lysts and new insights on the mechanistic aspects and product profiles. These features will help
readers find and retrieve information easily and straightforwardly and get a rational and historical
understanding of the state-of-the-art technology and knowledge. Overall, this book is an invaluable
resource for students and researchers in all laboratories working on catalysis, chemical synthesis
and medicinal chemistry, and it is likely to be the best monograph in the field for a long time.

Yoshiji Takemoto
Kyoto, February 2020

xiii
Taylor & Francis
Taylor & Francis Group
http://taylorandfrancis.com
Preface
Conjugated nitroalkenes are versatile substrates in organic synthesis because of their ability to par-
ticipate in a wide variety of reactions, including multicomponent and cascade reactions, primarily
due to the strong electron-withdrawing and coordinating ability of the nitro group. The easy acces-
sibility of nitroalkenes and the amenability of the nitro group to undergo diverse synthetic transfor-
mations have further strengthened the profile of nitroalkenes as promising substrates in both regio
and stereoselective synthesis of complex designed molecules and natural products. These unique
features of nitroalkenes have prompted synthetic organic chemists to employ nitroalkenes as sub-
strates in catalytic asymmetric reactions. Over the past two decades, numerous chiral metal-based
and organocatalysts have been employed in various asymmetric reactions involving nitroalkenes
not only toward developing new methodologies but in targeted synthesis as well.
Over 25 reviews have appeared in the literature since 2002 on various catalytic asymmetric
reactions of nitroalkenes. However, while those excellent reviews have highlighted different facets
of nitroalkenes, a comprehensive coverage of the multifaceted reactivity of nitroalkenes in cata-
lytic asymmetric reactions was probably beyond the scope of a journal review or a book chapter.
Therefore, we felt that synthetic organic chemists and medicinal chemists interested in nitroalkene-
derived enantioenriched molecules with key functional groups and potential bioactivity would ben-
efit if a systematic compilation of various asymmetric synthetic methods involving nitroalkenes as
substrates in the presence of various chiral catalysts developed till date is available in one place.
New insights into the mechanistic aspects and stereoselectivity could be of interest to physical
organic chemists as well as theoretical chemists.
This book begins with a brief introduction to the catalytic asymmetric reactions of nitroalkenes
with reference to the journal reviews and the book chapters that have appeared in the literature
thus far. This is followed by a chapter-wise description of the reactivity of nitroalkenes in Michael
addition, cycloadditions and cascade reactions (see Introduction). We have made every effort to
include all the reagents and reaction conditions in the schemes. Further, the number of examples,
product yield, diastereomeric ratios and enantiomeric excess have also been included. Although the
mechanism is discussed in the text in most cases, the detailed mechanistic schemes are included
only in selected cases. However, all available transition state models are presented and discussed to
rationalize the observed stereoselectivity. Over 650 articles, including reviews, have been covered
in this book. But if there are any omissions, we apologize in advance and promise to include them
in the next edition.
We are deeply grateful to Prof Takemoto who is a pioneer in the arena of asymmetric catalysis for
writing a foreword to this book. We are highly indebted to Prof Viswakarma Singh for patiently and
critically reading all the chapters and giving his valuable suggestions and comments. We sincerely
thank our group members Pallabita Basu, Sonia Naik and Nikil Purushotham for proofreading the
manuscript. We also thank the editor Dr Renu Upadhyay and her associate Ms Jyotsna Jangra for
their guidance and support. Finally, INN thanks his wife Jayasree and daughters Ashcharya and
Susmrithi for allowing him to spend extended hours in his office to complete this book.

Irishi N. N. Namboothiri
Meeta Bhati
Madhu Ganesh
Basavaprabhu Hosamani
Thekke V. Baiju
Shimi Manchery
Kalisankar Bera
February 2020

xv
Taylor & Francis
Taylor & Francis Group
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Authors
Irishi N. N. Namboothiri received his MSc from Mangalore University and PhD from the Indian
Institute of Science, Bangalore. He did his postdoctoral research at Bar-Ilan University, Israel,
University of North Texas and Columbia University. After a brief stint as a Senior Research Scientist
at Sabinsa Corporation, New Jersey, he joined the Department of Chemistry, IIT Bombay where
he is currently a professor. His research interests include organic synthesis, development of new
synthetic methodologies, asymmetric catalysis, mechanistic studies and materials chemistry. He
is an elected fellow of the Indian Academy of Sciences and National Academy of Sciences India.
He is also a recipient of the Chemical Research Society of India Bronze medal. He has supervised
over 20 PhDs and co-authored over 155 publications including two chapters and a book and is also
a co-inventor of six patents.

Meeta Bhati was born in Jaipur, Rajasthan, India in 1990. She received her BSc degree (2011) from
Maharani’s College, University of Rajasthan, Jaipur. She joined the Central University of Rajasthan,
Ajmer for an MSc degree in Chemistry (2013), and has also completed her PhD in Organic Chemistry
(2013–2019) in the same institution under the guidance of Dr Easwar Srinivasan. A year ago, she
joined as an Institute Postdoctoral Fellow with Prof I. N. N. Namboothiri, IIT Bombay (2019). Her
research interest is focused on designing asymmetric organocatalysts for enantioselective reactions
using sustainable catalytic protocols and “on-water” organocatalyzed reactions.

Madhu Ganesh obtained his MSc from Mangalore University in 2000 and PhD degree from IIT
Bombay in 2007. His doctoral work under Prof I. N. N. Namboothiri was on probing stereoselec-
tive reactions of nitroalkenes. He undertook postdoctoral studies at Rutgers University, New Jersey
and City College, New York. He worked in the industry as a Scientific Associate (2000–2002) and
further as a Research Investigator (2010–2013) at Syngene International Pvt. Ltd. After working as
an Assistant Professor in the Department of Chemistry, B M S College of Engineering, Bengaluru,
since 2013, recently he joined as an Associate Professor in the Department of Pharmaceutical
Technology/Process Chemistry, National Institute of Pharmaceutical Education & Research,
Hyderabad. His research interests include the development of synthetic methods and their applica-
tions in the pharmaceutical industry.

Basavaprabhu Hosamani was born in Raichur, Karnataka, India in 1986. He received his BSc
(2006) and MSc (2008) degrees in Chemistry from Bangalore University. He earned his PhD degree
from Bangalore University under the supervision of Prof V. V. Sureshbabu in May 2014. After a
brief stint as an Assistant Professor at an Engineering college, he worked as an Institute Postdoctoral
Fellow with Prof I. N. N. Namboothiri, IIT Bombay (2015–2017) and as a DST-SERB National
Postdoctoral Fellow at the Central University of Karnataka with Dr K Hanumae Gowd (2017–2018).
After serving as an Assistant Professor at the HKE Society’s SLN College of Engineering, Raichur,
Karnataka during 2018–2019, he joined as a Scientific Officer at the Regional Forensic Science
Laboratory, Kalaburagi, Karnataka. His research interests include organocatalytic asymmetric syn-
thesis, synthesis of modified nucleosides and some biologically active molecules.

xvii
xviii Authors

Thekke V. Baiju was born in Kasaragod, Kerala, India in 1987. He received his BSc (2007) and
MSc (2009) degrees in chemistry from Kannur University, Kerala. He completed his PhD work in
organic chemistry from CSIR-NIIST, Thiruvananthapuram. Until recently, he worked as an Institute
Postdoctoral Fellow with Prof I. N. N. Namboothiri, IIT Bombay. Currently, he is an Assistant
Professor at Government Brennen College, Thalassery, Kerala. His research interest is focused
on the synthesis of carbo- and heterocyclic scaffolds by multicomponent and cascade reactions of
functionalized nitroalkenes.

Shimi Manchery received her BSc degree in Chemistry from Calicut University and MSc
degree from Mahatma Gandhi University, Kerala. She completed PhD from CSIR-NIIST,
Thiruvananthapuram, Kerala. Until recently, she worked as a Senior Research Fellow with Prof I.
N. N. Namboothiri, IIT Bombay.

Kalisankar Bera received his BSc degree in Chemistry from Haldia Government College affiliated
to Vidyasagar University, West Bengal in 2006 and MSc degree in Chemistry from IIT Madras in
2008. He completed his PhD at IIT Bombay under the supervision of Prof I. N. N. Namboothiri and
postdoctoral work at the University of Leipzig, Germany, and Vanderbilt University, United States.
Currently, he is a Research Scientist at Syngene International Pvt. Ltd, Bengaluru. His research
includes organocatalytic asymmetric reactions for enantioselective synthesis of multifunctional
molecules.
Introduction

In the past 20 years, asymmetric catalysis has emerged as a powerful technique to synthesize
enantiomerically enriched compounds that are required to achieve potency and selectivity in biol-
ogy and medicine. This is due to the difficulties associated with accessing complex natural products
of pharmaceutical relevance that contain chiral centers via the resolution of racemic mixtures or
via synthesis using traditional chiron and auxiliary approaches. The increasing demand for such
molecules with complex, diverse and desirable properties necessitated the development of innova-
tive and economical methods, particularly involving catalysis, such as organocatalysis,1–34 metal
catalysis35–48 or biocatalysis.49–53
Nitroalkenes are excellent Michael acceptors because of their ability to undergo facile addition
of various C-, O-, N-, and S-centered nucleophiles. Michael adducts are key precursors to complex
molecules, including natural products (Figure 1).54 Nitroalkenes also participate as dienophiles and
heterodienes in Diels–Alder reactions, as dipolarophiles in 1,3-dipolar cycloadditions, as well as
substrates in Morita–Baylis–Hillman and Rauhut–Currier reactions. The nitro group is also ame-
nable for transformation to various functional groups, such as hydroxylamine, amine,55 etc., and is a
masked carbonyl exhibiting umpolung reactivity.56 Because of their versatile reactivity, nitroalkenes
are often referred to as “synthetic chameleons” in organic synthesis.57–63

Cl

CO2H
O O
NH2.HCl NH2
NH2.HCl HO
HO
(R)-Baclofen (S)-Phenibut Pregabalin
MeO MeO
O

O OMe O
OH HO2C

O O n-Pr
N N
HN
O OMe CONBu2
PDE4 Inhibitor (IC86518) (R)-Rolipram Endothelin-A antagonist
(ABT-546)
N
O
O EtO2C O
F N 11
CH3
NHAc
HO O NH2 F
11
(-)-Botryodiplodin (-)-Oseltamivir F (R)- C-UCB-J

FIGURE 1 Selected biologically active molecules synthesized from nitroalkenes via asymmetric catalysis.

1
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2 Catalytic Asymmetric Reactions of Conjugated Nitroalkenes

Nitroalkenes have become the benchmark substrates in asymmetric catalysis due to their above-
mentioned reactivity profile. Catalytic asymmetric reactions of nitroalkenes have made rapid progress
generating tremendous knowledge not only on synthetic strategies and tactics but also on products
with diverse functionalities and biological activities. However, there has been no comprehensive
literature on asymmetric reactions of nitroalkenes. A review on asymmetric Michael additions of
nitroalkenes was published by Enders way back in 2002.64 Later in 2017, Alonso and co-workers
published a review on asymmetric organocatalytic conjugate additions to α,β-unsaturated nitro com-
pounds, which covered only the reactions under organocatalytic conditions.65 Several authors have
described selected asymmetric reactions of nitroalkenes as such or as a part of their review focusing
on other chemistry. For example, in a review of organocatalyzed transformations of β-ketoesters
by Naicker et al., reactions with nitroalkenes were also described.66 We also published a series of
reviews on the application of nitroalkenes in the synthesis of carbocycles and heterocycles,67–69
as well as on the Morita–Baylis–Hillman reaction of nitroalkenes70,71 where certain asymmetric
reactions were alluded. Besides, several reviews have been published on the asymmetric reactions
of nitroalkenes, such as Michael addition,39,64,72–77 cycloadditions,78–81 Friedel–Crafts alkylation82–84
and multicomponent cascade or domino reactions,85–87 as well as applications of such asymmetric
reactions in the synthesis of various carbocycles, heterocycles74,82,83,88,89 and total synthesis.90
We felt that synthetic organic chemists and medicinal chemists interested in enantioenriched
molecules with key functional groups and potential bioactivity would be of benefit if a systematic
compilation of various asymmetric synthetic methods involving nitroalkenes as substrates in the
presence of various chiral catalysts developed to date is available in one place. New insights into
the mechanistic aspects and product profiles are also covered in this book. The book begins with
catalytic asymmetric Michael additions of various carbonyl compounds to nitroalkenes. This is
followed by catalytic asymmetric Friedel–Crafts reactions of nitroalkenes with indoles, pyrroles
and electron-rich phenols. Subsequently, catalytic asymmetric Michael addition of other carbon-
and heteroatom-centered nucleophiles to nitroalkenes and cycloadditions such as 1,3-dipolar
cycloaddition, [2+2]-, [3+2]- and [4+2]-cycloadditions of nitroalkenes are discussed in detail.
Catalytic asymmetric reduction and various cascade reactions are dealt with in the latter part of
this book.

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Taylor & Francis
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the extent which is essential to us. The two Delegations have,
however, already arrived at an agreement on most of the questions
which have been the subject of reciprocal demands, and now certain
controversies remain to be solved which, although they offer the
greatest interests for both sides, it is to be hoped may be solved
with satisfaction to all.
Special attention has been paid by the two Delegations to the
study of the questions relative to the traffic through the port of
Trieste and the regulation of the frontier traffic for the protection of
the interests of the populations of the zone near the frontier of the
two States. On this subject agreement may be said to be complete.

The Commercial Treaty with Yugoslavia. The negotiations with

Yugoslavia, which should lead to the regulation of all the economic
and financial questions still pending between the two States, have
been conducted so far on the Treaty of Commerce, which, except for
the part concerning the Italian proposals on the tariffs, may be said
to be already agreed upon by the two Delegations. With reference to
the other subjects under examination, of which only a small part has
been possible to discuss at the same time as the negotiations for the
Commercial Treaty, the Yugoslav Delegation is now awaiting further
instructions from Belgrade. Besides the commercial negotiations I
have mentioned, there are others proceeding for a Commercial
Treaty with Spain. Negotiations will shortly be opened for
commercial agreements with Siam, Finland, Esthonia, Lithuania,
Lettonia and Albania.
(After a short discussion, in which several Ministers participated,
the Cabinet approved the declarations of the Prime Minister.)
 “MINE IS NOT A GOVERNMENT WHICH
DECEIVES THE PEOPLE”
Speech delivered at the Palazzo Municipale on 2nd June 1923, to the contadini of
Rovigo.

Fascisti,—How shall I find adequate words to thank you for this

magnificent welcome? A few moments ago your mayor gave voice to
the greeting of the city and the province. To-day I have passed
through your fertile lands, furrowed by rivers, exploited by your
tenacious work. All Italy must be grateful to this industrious people,
who, too, having realised the beautiful and supreme interests of the
nation, has now all the more the right to be treated with greater
friendship and consideration.
I know that I am speaking to an assembly where workers are
certainly in enormous majority. Well, I say to them with calm words
and with a still calmer conscience that the Government which I have
the honour to represent is not, cannot, and will never be against the
working classes. (Loud applause.) Six months of Government are still
too few for a programme to be carried through, but, to my mind,
they are sufficient to give an idea of its directives which to-day are
precise and sound. Mine is not a Government which deceives the
people. (Applause.) We cannot, we shall not, make promises if we
are not mathematically sure of being able to fulfil them. The people
have been too long deceived and mystified for the men of our
generation to continue this low trade.
We have traced a furrow, very clear-cut and deep, between that
which was the Italy of yesterday and that which is the Italy of to-
day. In the latter, all classes must have a sphere of action for their
fruitful co-operation. The struggle between classes may be an
episode in the life of a people, it cannot be the daily system, as it
would mean the destruction of wealth, and, therefore, universal
poverty. The co-operation, citizens, between him who labours and
him who employs labour, between him who works with his hands
and him who works with his brains, all these elements of production
have their inevitable and necessary grades and constitutions.
Through this programme you will attain a state of well-being and the
nation prosperity and greatness. If I were not sure of my words I
would not utter them before you on such a solemn and memorable
occasion. (Applause.)

(At this point of the speech an aeroplane piloted by Ferrarin was

executing some daring evolutions just above the Palazzo Municipale,
from where Mussolini was speaking. The Prime Minister stopped for
a few seconds following Ferrarin’s evolutions, then went on:)

Fascisti! The other day I was passing in one of those aeroplanes

over your town. That flight was profoundly significant, as it was
meant to show that six months of tenure of office have not yet
nailed me down into my Presidential easy chair and that I, as you, as
all of you, am still ready to dare, to fight, if necessary, to die, so that
the fruits of the great Fascista revolution may not be lost!
Long live Fascismo! Long live Italy! (Loud applause.)
“IN TIME PAST AS IN TIME PRESENT, WOMAN
HAD ALWAYS A PREPONDERANT INFLUENCE
IN SHAPING THE DESTINIES OF HUMANITY”
Speech delivered at Padua at the first Women’s Fascista Congress, on 2nd June
1923.

Ladies,—If I am not mistaken, this, which is inaugurated here to-

day, is the first Women’s Fascista Congress of the “three Venices.”
The title and the field covered by this first Congress of yours are full
of profound significance. Fifty years ago one could not speak of the
“three Venices”! Venice herself, after the magnificent years of
heroism of 1848 and 1849, was still held by the shackles of foreign
slavery. In 1866 we liberated Venice, one of the Venices. Fifty years
afterwards we liberated the other two—that which has as its
boundary the devoted and impregnable Brenner, and the other
which has as its boundary the not less devoted nor less impregnable
Nevoso.
Fascisti do not belong to the multitude of fops and sceptics who
mean to belittle the social and political importance of woman. What
does the vote matter? You will have it! But even when women did
not vote and did not wish to vote, in time past as in time present,
woman had always a preponderant influence in shaping the destinies
of humanity. Thus the women of Fascismo, who bravely wear the
glorious “black shirt,” and gather round our standards, are destined
to write a splendid page of history, to help, with self-sacrifice and
deeds, Italian Fascismo.
Do not trust the little stuffed owls, the yelling monkeys or, indeed,
any representative of the lower zoological orders, who believe they
practise politics, but could be called by a more infamous name. Do
not believe those who talk of crises within the ranks of Fascismo;—
these are details, mere episodes in the great event, and they, after
all, concern men, not masses. When Fascisti have not to strike the
enemy, they can well afford themselves the luxury of internal
quarrels. But if the enemy should begin to raise his head again and
intensify the character of his more or less stupid opposition, then
Fascisti will again become solidly united. Then “Woe to the
vanquished!” (Applause.) And since the opportunity is propitious, I
would like to tell you, women of Fascismo, and the Fascisti of all
Italy, that the attempt to sever Mussolini from Fascismo or Fascismo
from Mussolini is the most useless and grotesque attempt that could
be conceived. (Applause.) I am not so proud as to say that I who
speak and Fascismo are one; but four years of history have now
clearly shown that Mussolini and Fascismo are two aspects of the
same thing, are two bodies and one soul or two souls in a single
body. I cannot forsake Fascismo, because I have created it, I have
reared it, I have strengthened and I have chastened it, and I still
hold it in my fist, always! It is, therefore, quite useless for the old
screech-owls of Italian policy to pay me their foolish court. I am too
shrewd to fall into this ambush of the commercial mediocrities of
village fairs. I can assure you, my dear friends, that all these little
vipers, all these cheap politicians will be bitterly disillusioned.
To think that I could become brutalised in Parliamentary
bureaucracy is to believe an absurdity. Although I come from the
working class, I have a spirit too aristocratic not to feel disgust for
low Parliamentary manœuvres. We shall continue our march
vigorously (added the Hon. Mussolini, raising his voice), because this
has been imposed on us by destiny. We shall not turn back, nor shall
we even mark time. I have already said that we did not want to
push matters to extremes only to see ourselves driven back by the
swing of the pendulum. I prefer, as I wrote in an article, which
aroused some interest—I prefer to march on continually, day by day,
in the Roman way, in the way of Rome who is never reconciled to
defeat; of Rome who welcomed Terentius Varro coming from
Cannæ, although she knew that he had given battle against the
opinion of Consul Paulus Æmilius and was, in a certain degree,
responsible for the defeat; of Rome who after Cannæ forbade
matrons to sally forth, so that their grief-stricken bearing should not
shake the strength of the citizens; of this Rome who re-wrote
continually the chapters of her history, who found in every ill-success
the incentives to endurance, to steadfastness, to strengthen her
spirits, to harden her nerves, to light the flame of passion! This is
the Rome of whom we dream; the Rome in whom all hierarchies are
respected, those of strength, beauty, intelligence, and human
kindness; the Rome who struck hard at her enemies, but then raised
them up again and made them share her great destiny; the Rome
who left the utmost liberty to the beliefs of her subject-peoples,
provided only that they obeyed her!
Giuseppe Mazzini used to say that power is but the unity and
perseverance of all efforts put together. Well, Italian power, Fascista
power, the power of all the new generations which expand in this
superb spring of our life and history, will be the result of the unity of
our efforts, of the tenacity of our work. After all, what do Fascisti ask
for? They are not ambitious or factious. They have the sense of
limitation and of their responsibility. And I am sure of interpreting
your thought, the deep craving of your soul, if I say that Fascisti,
from the first to the last, from the leaders to the led, ask only one
thing: To serve with humility, with devotion, with steadfastness, our
beloved Mother Country, Italy! (The speech was greeted with
enthusiastic applause.)
 “SO LONG AS THESE STUDENTS AND THESE
UNIVERSITIES EXIST, THE NATION CANNOT
PERISH AND BECOME A SLAVE, BECAUSE
UNIVERSITIES SMASH FETTERS WITHOUT
ALLOWING THE FORGING OF NEW ONES”
Speech delivered at the University of Padua on 3rd June 1923.

Mr. Chancellor, Professors, My Young Friends,—It is not I who

honour your University, it is your University which honours me, and I
must confess that, although on account of my laborious dealings
with men I am a little refractory to emotions, to-day, being among
you, I feel deeply touched.
We have known each other for some time, from 1915, from the
days of that May always radiant. I remember that the students of
Padua hung up at the doors of this University a big paper puppet
representing a politician about whom I do not wish to express any
opinion now. But that act meant that the youth of the University of
Padua did not want to hear about ignoble diplomatic bargains—
(Applause.)—did not want to sell its splendid spiritual birthright for a
more or less wretched mess of pottage. The University of Padua, the
students, who were not degenerate descendants of those Tuscan
students who went out to die at Curtatone and Montanara, wished
then to be the vanguard, to take up their post in the fighting line,
carrying with them the reluctant ones, chastening the pusillanimous,
overthrowing the Government and going out to fight, to sacrifice and
death, but also to honour and glory.
From that time I know that among you there are faithful followers
and that this University among all the others is truly an active centre
of faith and of intense patriotism. If I look back for a moment to the
rolling by of centuries, I recognise in this University a great fountain
at which thousands of men of all countries, of all generations, of all
races, have quenched their thirst.
The Government which I have the honour to represent repudiates,
at any rate in the person of its chief, the doctrine of materialism and
the doctrines which claim to explain the very complex history of
humanity only from the material point of view, to explain an episode,
not the whole of history, an incident, not a doctrine. Well, this
Government prizes individual, spiritual and voluntary qualities, holds
in high esteem the Universities, because they represent so many
glorious strong points in the life of the people. In fact I do not
hesitate to state that if Germany has been able to resist the powerful
influence of Bolshevism, it is due, above all, to the strong University
traditions of that people.
A people with an ardent spirit and with genius like ours is
necessarily a well-balanced and harmonious one. The Government
understands the enormous historic importance of Universities, has a
respect for their noble traditions and wishes to raise them to the
heights of modern exigencies. All this cannot be done at once, as
everything cannot be accomplished in six months. All that we are
doing at present is to clear the ground from all the débris which the
rotten political caste has left us as a said inheritance. (Applause.)
How could a Government composed of former soldiers ever
disparage Universities? It would not only be absurd but criminal!
From the Universities have come out by the thousands volunteers
and by tens of thousands those magnificent warriors who used to
assault the enemy’s trenches with a superb contempt of death. They
are our comrades whose memory we bear engraved in our hearts.
You will write their names on your gates of bronze, but their memory
will be more imperishably engraved in our spirit. We cannot forget
them, as we cannot forget that out of the Universities came by
thousands the “black shirts,” those “black shirts” who, at a given
moment, put an end to the inglorious vicissitudes of Italian politics,
who took by the throat with strong fingers all the old profiteers who
appeared, to the exuberant impatience of the new Italian
generations, always the more inadequate for their paralysing
decrepitude. (Applause.) Well, so long as there are Universities in
Italy—and there certainly will be for a long time—and so long as
there are young men to attend these Universities and to become
acquainted with the history of yesterday, thus preparing the history
of to-morrow, so long as there are such young men, the doors of the
past are definitely shut. I guarantee it formally! But I add further
that so long as these young men and these Universities exist, the
Nation cannot perish and it cannot become a slave, because
Universities smash fetters without forging new ones. (Applause.) If
to-morrow it were again necessary, either for causes arising within
or without the frontiers, to sound again the trumpet of war, I am
sure that the Universities would again empty themselves to re-
populate the trenches. (Loud applause.)
And now that you have rejuvenated me by twenty years, I would
like to sing with you the “Gaudeamus Igitur.” After all, Lorenzino dei
Medici was right when he sang: “How beautiful is youth!” Well, my
young friends, there can never be for us as individuals the certainty
of the morrow, but there is the supreme and magnificent certainty of
the morrow for us as a nation and as a people.
And with the students’ hymn, let us utter in Latin a simpler word,
Laboremus. To work with dignity, with probity and with cheerfulness,
to assault life with earnestness and to meet it as a mission, trying to
fulfil the categorical injunction left us by our dead. They command
us to obey and to serve, they command us discipline, sacrifice and
obedience.
We should really be the last of men if we failed to do our clear
duty. But we shall not fail. I who hold the pulse of the nation and
who carefully count its beats, I who sometimes shudder in the face
of the heavy responsibilities which I have assumed, feel in me a
hope, nay a vibration, of a supreme certainty which is this: that, by
the will of the leaders, by the determination of the people, and by
the sacrifice of past, present and future generations, Imperial Italy,
the Italy of our dreams, will be for us the reality of to-morrow. (Loud
applause.)
 ITALY’S FOREIGN POLICY REGARDING
GERMAN REPARATIONS, HUNGARY,
BULGARIA, AUSTRIA, YUGOSLAVIA, TURKEY,
RUSSIA, POLAND AND OTHER COUNTRIES
Speech delivered at the Senate on 8th June 1923.

Honourable Senators,—The speech that I have the honour of

delivering before your illustrious Assembly may appear analytical,
because in it I propose to touch on several questions and to speak
decisively upon several problems, especially with regard to internal
policy.[13] By this I do not delude myself to be able to convince those
who are my opponents in malâ fide, nor to disperse completely the
small opposition which nourishes itself on detail, and is the effect of
personal temperament.
13. The speech on Internal Policy here referred to will follow this one on page
306.
You will not be surprised if I begin with foreign policy, even if it
happens that this is the field in which serious and founded
opposition does not exist, and it may be legitimately said that our
policy is endorsed unanimously by the nation.
As I have already said on other occasions, the foreign policy of the
present Government is inspired by the necessity for a progressive
revaluation of our diplomatic and political position in Europe and in
the world. It is a fact that, except for territorial acquisitions bounded
by the Brenner and the Nevoso, frontiers wrested by long and
bloody wars, Italy was excluded in the Peace of Versailles and other
successive treaties from all other benefits of an economic and
colonial nature. Solemn pacts signed during the war have lapsed and
have not been replaced. The position of inferiority assigned to Italy
has weighed and still weighs heavily on the economic life of our
people. It is useless to dwell upon recriminations of the past. We
must rather seek to regain the ground and time lost. There is no
doubt that from October to to-day the situation has notably
improved.
The other Powers, whether allied or not, know that Italy intends
to follow an energetic and assiduous policy for the protection of her
natural and vital interests, intends to be present wherever, directly or
indirectly, they are at stake, because this is her right and her definite
duty; but at the same time she is in favour of that line of conduct in
general policy which tends to bring back as quickly as possible to a
normal state the economic situation of our continent. Italy, who too
is marching rapidly towards her readjustment, sees this re-birth
continually disturbed by general outside factors. There is, therefore,
a definite Italian interest in hastening the pacific solution of the
European crisis.

The Position of Italy and Reparations. All such crises, since the
Treaty of Versailles onwards, have been dominated by the one
problem: Reparations. In the face of this problem the fundamental
position of Italy is as follows:
1. Germany can and must pay a sum which now seems universally
fixed and which is very far from the many hundreds of milliards
talked of on the morrow of the Armistice;
2. Italy could not tolerate territorial changes which would lead to a
political, economic or military hegemony in Europe;
3. Italy is prepared to bear her quota of sacrifice, if it is necessary
to obtain what is called European reconstruction;
4. The Italian Government maintains to-day more than ever, above
all after the last German Note, that the problem of reparations and
that of Inter-Allied debts are intimately connected and are in a
certain sense interdependent.
 There is no doubt that the occupation of the Ruhr has contributed
to render the crisis of the Ruhr extremely acute, and therefore to a
certain extent hastened a solution.
It will not be inopportune to recall, considering the rapidity of
events, that the French and Belgians went to the Ruhr on account of
the declarations of a series of failures of the supplies in kind by
Germany, admitted also by England, at any rate as regards that of
wood, and the failure of the Conference of Paris.
It is certainly worth while to fix exactly in their essential lines the
main features of the Italian, English and German projects, in order
to have a picture of the situation as regards its agreements and
divergencies, and to see what conjectures we can form as to a
possible settlement. This will also serve to explain why Italy was not
able to accept the Bonar Law scheme at Paris, and why she had to
reject the recent Cuno-Rosenberg Memorandum.
The Italian project reduced the German debt to fifty milliards of
gold marks, proposed a moratorium of two years, during which
Germany would continue the supply of reparations in kind, accepted
the distribution of German payments according to the quotas fixed
at Spa, by which the Italian quota was put at five milliards of gold
marks, fixed the payment of one part of the “C” bonds by means of
the security given by the other ex-enemy States, used the remainder
of the “C” bonds to settle the debt to America, agreed to the taking
of economic pledges as a guarantee of the German payments, and
finally, as regards the payments of the reparations owed by Austria,
Bulgaria and Hungary, asked for a pledge for the acceptance of the
proposals which England had deferred putting forward—proposals,
that is, of annulling those debts.
The Italian quota of reparations, which the Italian project fixed at
five milliards of gold marks, was thus reduced in the English project
to less than half; whilst cancelling the bonds, it partly abolishes to
our detriment German solidary responsibility for minor ex-enemy
debts and rendered impossible the execution of the agreement of
March 1921, which ensures important advantages to Italy upon the
basis of the “C” bonds. The larger percentage reserved on the
seventeen milliards, representing the interest of the moratorium
capitalised to 1923, could not be used for the payment of American
debts, in consideration of the aleatory nature of these seventeen
milliards.
I do not recall all this to reopen discussions, but only to make
clear the main outlines of that which was and remains a noteworthy
attempt to find a solution for this grave problem; an attempt which
contains worthy elements which can be usefully taken up again in
case of a definite settlement.
The conclusion of an agreement between England and America on
the problem of debts—the work of the then Chancellor of the
Exchequer, Mr. Baldwin, to-day Prime Minister, followed shortly after
the presentation of the English project.
Any idea of this debt being itself cancelled, or even of a simple
compensation through the payment of reparations, is excluded from
this agreement. The obligation to pay, although facilities may be
accorded concerning both the number of years in which it must take
place and the interests due, is solemnly affirmed and put into
execution. In England the Speech from the Throne strongly
emphasised this agreement. Even taking into account the diversity of
economic strength and the totality of sacrifices borne, it could not
remain without effect upon the importance of the whole question for
the other European Powers.

Analysis of the German Project. If we compare the English and

Italian projects with the German, the inacceptability of the latter
appears evident. As is known, one of the fundamental points of the
last German project concerns the consolidation of the actual debt of
Germany, especially in kind, at the figure of twenty milliard gold
marks, with an additional ten milliards, the payment of which
depends upon the decision of an International Commission.
Deducting the interest, these twenty milliards are reduced to fifteen,
and the sums necessary must be found by international loans; and
in the very probable eventuality that by 1927 the twenty milliards
have not been subscribed, an annuity will be paid which represents
five per cent. interest plus one per cent. for the redemption of the
loan. Finally, in the German project any provision or regulation for
the guarantees demanded is lacking. The total German debt, which
in the English and the Italian projects is fixed at the figure of fifty
milliards, in the German project is reduced to less than a third, and it
is difficult, if not impossible, to determine in it the Italian quota and
the sacrifice demanded from Italy.
In view of the representations, especially of England and Italy,
Germany has recognised her proposals as insufficient, and yesterday
the German Ambassador, Neurath, presented to me the new German
Note, on the contents and nature of which I cannot pronounce an
opinion for evident reasons, as in consequence of this Note
diplomatic action with all the Allies must be taken up. I will only say
that the German Note no longer demands the preliminary evacuation
of the Ruhr as a condition for negotiation. This might make us
believe in a renunciation on the part of Germany of that passive
resistance, the utility of which—even for German aims—appears ever
more doubtful, and whose cessation would help towards a more
rapid attainment of a solution.

Italy and Hungary. But the problem of reparations is not only

Franco-German, it is also Hungarian, Bulgarian and Austrian.
It is useful to define the stage which has been reached with
regard to these ex-enemy countries. The total of the Hungarian
reparations, which is fixed by the Treaty of Trianon, has not yet been
determined by the Reparations Commission, and Hungary up to to-
day has only furnished limited supplies in kind. The Hungarian
Government, alleging the disturbed economic and financial
conditions of the country caused by the serious depression of the
krone, has recently put forward the necessity to contract a foreign
loan, which, if it is to succeed, should be guaranteed by the custom
duties, by the tobacco monopoly, and, if needs be, by other
resources. Hence arises the necessity for such resources to be freed
for an adequate period from the claims of reparations. A
Memorandum precisely to this effect has been recently presented by
the Hungarian Minister in Paris to the Reparations Commission.
The Italian Government, having examined the question from a
technical point of view, has deemed it indispensable to concede to
Hungary the temporary relinquishment of certain resources, so that
she may proceed to her own economic restoration by means of loans
to be contracted abroad. Italy has, therefore, shown herself
favourable to the above Hungarian request, with the addition of
certain conditions necessary to guarantee her own rights, on which
point she is in agreement with the British Government.

Agreement with Bulgaria for Payment. With reference to Bulgarian

reparations, Italy, Great Britain and France came to an agreement on
21st March with the Bulgarian Government to facilitate the payment
of her debt of 2250 million gold francs fixed by the Treaty of Neuilly,
by dividing it in two parts; one of 550 millions to be paid by
instalments beginning in October of this year, and the other 1700
millions not to be claimed before thirty years.
Bulgaria has pledged herself by this agreement to reserve for the
regulation of her debt the revenues of her customs and has already
passed a law to this effect. The agreement has also been approved
by the Reparations Commission, with the reservation of our rights for
the reimbursement of the expenses of the army of occupation. In
fact, negotiations are proceeding with the Bulgarian Government for
the regulation of this credit, which enjoys the privilege of priority
over other reparations.
Our Government, animated by favourable dispositions as regards
all that concerns the settlement of obligations arising from the war,
has had no difficulty in accepting such an agreement.

The Loan to Austria. Fulfilling the pledge taken by its predecessors

in the Protocol of Geneva of 4th October 1922, the Italian
Government has co-operated with the Governments which are
signatories of the Protocol, in order that the loan in favour of Austria
should have a large and ready success. For this purpose the
Government has consented to postpone for twenty years, which is
the duration of the War Loan, her credits against Austria for the
recovery of damages and for bonds of food supply, has given her
own guarantee for twenty-five per cent. of a maximum loan of 585
million gold kronen, and has authorised Italian banks to contribute
directly to the loan up to the maximum of 200 million lire, including
the sixty-eight which Italy had previously lent to Austria, and which,
by the terms of the Protocol of Geneva, should have been repaid in
cash.
Putting off for a further period the exaction of Austrian reparation,
and giving a guarantee and a direct and substantial contribution to
the loan in favour of Austria, the Italian Government has wished to
offer her co-operation towards the political independence and
territorial integrity of the Austrian Republic to which the Protocol of
Geneva refers, and to which the United States of America also wish
to contribute, confidently subscribing for the first time to a European
loan.

Relations between Italy and Yugoslavia. Italy’s political line of

conduct towards the States of the Little Entente and in general
towards the States recently created is substantially inspired by the
necessity of exacting the respect and the scrupulous fulfilment of the
treaties, because, given the present contingencies, only such a
policy can produce quick and pleasing results with regard to an
economic settlement of the Danubian States which would contribute
to the larger one of Central Europe. On several occasions the friendly
and moderate policy of Italy has followed such a course with
satisfactory results.
With reference to such a policy the relations between Italy and
Yugoslavia have a special importance. The clear attitude taken by
the Government with regard to Yugoslavia by proceeding to the
definite enforcement of the Treaty of Rapallo has strengthened our
legal position, and we are able to rest any further development of
our policy on a solid basis. The enforcement of the Agreements of
Santa Margherita, which has been necessarily laborious owing to the
large extent of the field covered, can be said, however, to proceed
on the whole satisfactorily. In spite of the initial difficulties
encountered in any exceptional régime, the economic system of the
so-called “special zone of Zara” is already in force for the evacuation
of the remaining Dalmatian territories, and the various organisations
for the regulation of all the intricate questions arising out of the
Agreements have been constituted.

Fiume. But naturally the most important question to solve is that

of Fiume. As is known, it offers the gravest difficulties, since, in
order to ensure the future of the commercial life of the town, there
must be solved many complex problems of an economic nature
which are often in opposition to those of a political character.
Undoubtedly the recent long Parliamentary crisis in Yugoslavia,
which for a considerable time forced the Government of Belgrade to
confine its attentions almost exclusively to internal problems, has
heavily weighed against the rapidity of the solution of such a
question.
That Government has repeatedly acquainted us with its wishes to
solve the question in a satisfactory way as regards the sentiments
and the interests of Italy, and has also frankly made known to us the
real difficulties with which the Government is faced in asking the
populations interested to accept a solution in agreement with the
Italian point of view.

Italo-Yugoslav Commission. With a view to ensure an atmosphere

of greater quiet to the Italo-Yugoslav Commission, the Government
of Belgrade has, in the meantime, agreed to transfer the seat of the
Commission to Rome. The Yugoslav Delegation has arrived, and
between it and the Italian Delegation, which is fulfilling its duty with
a high sense of patriotism and political probity, preliminary meetings
are taking place with the object of fixing certain fundamental points
before resuming official discussions, so that the latter may proceed
with the necessary speed without lapsing into a deplorable
stagnation, which would be otherwise inevitable in such an arduous
task.

The Conference of Lausanne and the definite Cession of

Castelrosso to Italy. The Conference of Lausanne, which after the
well-known suspension of last February resumed its proceedings on
23rd April, is slowly completing them through the no small difficulties
of various kinds caused by the delicacy and complexity of the
questions under examination. The course followed by the Italian
Delegation under any circumstance has always been inspired by the
most calm and impartial attitude, and its efficacy has been
recognised and generally appreciated at its just worth.
Italy cannot help considering as her vital interests the speedy
restoration of a normal state of trade in the East, as well as the
economic development and general progress of all the peoples living
on the shore of the Eastern Mediterranean.
Although all the questions under discussion have not yet been
solved at Lausanne, on some of them, however, which more directly
affect our country, an agreement, satisfactory on the whole, has
been reached. The Government of Angora has explicitly withdrawn
the objection regarding the cession of the island of Castelrosso to
Italy, the possession of which on our part could in no way justify an
eventual suspicion of Italian aggressive aims with regard to Turkey.
Our flag, which has already been saluted from the moment it
appeared in the island as a symbol of peaceful well-being, will in the
future continue to protect a population which by plebiscite has
entrusted itself to us.

The Juridical Protection of Foreigners in Turkey. The Italian

Government has also obtained the cancellation of those clauses, with
regard to our colonies in North Africa, which the agreements
concluded after the Libyan War had left in existence, and at the
same time the interests of Libyan subjects residing in Turkey, whose
rights have been equal to those of Italian citizens, were opportunely
protected.
From the opening of the Conference the question of the juridical
protection of foreigners has been of the greatest importance. The
Conference has agreed in fixing the limits of such protection,
including it in a formula which establishes for a period of five years
the appointment on the part of the Turkish Government of foreign
judges, who are authorised to receive complaints of the sentences
and of the proceedings of Turkish magistrates.
At Lausanne there still remain under discussion certain important
questions of general interest, such as those relative to the
management of the Ottoman Public Debt and others of an economic
nature, which I hope may be quickly solved.

Relations between Italy and Russia. The present relations with

Russia are regulated by the Italo-Russian and Italo-Ukraine
Agreements of 26th December 1921. A few days ago the projects for
the conversion into law of the Royal Decree of 31st January 1922
were presented to Parliament, by whom the said agreements had
been approved, though some opposition had been offered to their
practical application. This opposition gave the Russians a pretext for
violating the agreement. We mean to remove these obstacles in
order to render easier the economic relations between the two
countries and pave the way for an understanding resting on a wider
basis without excessive illusions, but also without dangerous
prejudices.
Relations between the two countries, which possess different
economic systems, present enormous difficulties. They are, however,
not unsurmountable if on both sides there is a good-will to overcome
them. Italian policy towards Russia is clear and cannot give rise to
misunderstanding.
 The presentation before Parliament of these decrees represents
another proof of our intentions and gives us the right to expect from
the Government of Moscow the scrupulous fulfilment of the pacts,
the execution of the pledge taken to abstain from any act hostile to
our Government, and from whatsoever direct or indirect propaganda
against the institutions of the kingdom.

Relations between Italy and the United States. I do not think it is

necessary, considering the brevity of this speech, to enter into
further detail. I will only say that the relations between the United
States and Italy are particularly cordial, and I am glad to add that
both the Government and the American people have fully
understood the new political situation in Italy.

Relations with Poland and other Countries. The initiative of Italy

for the definite determination of the Polish frontiers has cemented
even more closely the bonds of cordial friendship which have united
the two countries for centuries. Their collaboration continues to be
strengthened on economic as well as on political grounds. In these
last days the Polish Government has placed important orders with
Italian manufacturers.
The conversations and the personal relations I have had with the
Ministers of Austria, of Roumania, of Hungary, the recent journey of
H.M. the King of England, the commercial treaties concluded and to
be concluded, are other signs of that progressive revaluation of our
diplomatic position which I referred to at the beginning of this
speech.

Improvement of the Diplomatic and Consular Services. The

Fascista Government, always with the object of this revaluation, as
soon as it came into power instructed its representatives abroad to
direct their policy outside the confines of the country to the renewed
life of Italy, and to face immediately the problem of the means and
the men for that end. In fact, the administration of Foreign Affairs, in
the face of so many difficulties from outside, already possessed a
great difficulty in her own constitution, due to the scanty number of
its elements. The tools of our work, which is so delicate abroad, had
to be renewed, and rendered suitable, as regards the increase in
number of officials and the new conditions of Italy, for the
momentous task which they are required to perform.
Instructions have, therefore, been given with effect from the first
days of November for the reorganisation of the competition for the
Diplomatic and Consular Services, and for Interpreters.
In conclusion I wish to repeat that Italian foreign policy, while it
intends to safeguard national interests, wants at the same time to
constitute a factor of equilibrium and peace in Europe, and by such a
policy I think I interpret the tendencies and the needs of the Italian
people. (Applause.)
 “THE INTERNAL POLICY”
Speech delivered at the Senate on 8th June 1923, after the one on Foreign Policy
(see p. 293).

Honourable Senators,—The problems of public order are problems

of the authority of the State. There is no real authority in the State if
public order is not perfectly normal. Public order and authority of the
State are, therefore, two aspects of the same problem. I ask you if
conditions have improved or become worse since last October.
(“Improved!”) Some of you give an affirmative answer. I, too, say
they have improved. Although, naturally, I am far from being
pessimistic and, therefore, from being discontented, I feel that
nothing ever goes well enough. But, Gentlemen, when one speaks of
public order, one must make comparisons. Even if they are
disagreeable, they are necessary. Unrest, uneasiness and sedition
are phenomena to be found not only in Italy. If we glance beyond
our frontiers we have reason to repeat that, if Messene weeps,
Sparta does not laugh! Look at the vanquished peoples and note
what happens in Austria and in Germany. Look at the victorious
peoples and you will see that only yesterday there was a strike of
public officials in Belgium, which has cost the Treasury hundreds of
millions of francs. If, then, you glance at the neutral countries, at
Spain, you will find there, too, that life is not excessively bright and
easy. All this I say for those who, at every small revolver shot fired in
one of the twenty thousand villages of Italy, think they have been
wounded by a 17–inch shell!

A Significant Comparison. But, above all, it is worth while to look

at Italy and consider, on one side, her conditions in the years 1918–
20 and in the period following 1920–21. The dominating events of
the former two years are the occupation of the factories, the
permanent strike of the officials belonging to public organisations,
carried out in rotation, and by a displacement of all the powers of
State authority (Assent.); and, although the incident is extremely
painful, one must recall to mind that in the rank and file of that
same glorious army of ours occurred an episode at Ancona which
proves how deeply sedition had worked its way into the body of the
Italian State.
The dominating event of the following two years is the punitive
Fascista expedition. Fascisti, from sheer necessity, went out to the
assault of the towns in large armed bodies. To-day all this is over.
To-day the officials of public organisations do not and will not strike.
(Assent.) When the Fascista employees of the Post and Telegraph
Offices came to me to protest because my colleague, the Hon.
Colonna di Cesaro, had punished them, I told them that if I had
been Minister of Post and Telegraphs I should have punished them
twice, and I added that, just because they were Fascisti, they would
have to recognise the necessity for a strict discipline. (Assent.)

The State renewed. The conditions of public order reached their

zenith of disintegration during the latter part of the year. In August
there was the anti-Fascista strike, which completely paralysed the
State. This had no effect; the Fascista forces, in its stead, obtained
success. And, from that time, I said that the two must be made one,
and that since that State was destitute of all the attributes of virility,
while there was a State in power which was rising with great
strength and capable of imposing discipline on the nation, it was
indispensable for the rising State to substitute itself, by a
revolutionary movement, for the other State which was declining.
The August anti-Fascista strike was followed by the Fascista
occupation of the towns of Bologna and Bolzano. The authority of
the State was a complete ruin. There are no more reports of labour
conflicts in the papers now.
 The Chamber and the Conflicts. I am sufficiently impartial to say
that in these last days there has been a slight recrudescence of
trouble. What is its cause? I tell you quite frankly: the reopening of
the Chamber. (Laughter.) The Chamber is the place of questions. By
the spectacle it offers to the nation it sows seeds of conflict and
discord amongst the impulsive and excitable masses.
Further, the attitude of a section of Italian Liberalism is a very
welcome piece of good fortune for the subversive elements, because
they constitute for them unhoped-for, unexpected allies, who blow
enormous bubbles, which I promise myself to prick with the pin of
logic and sincerity before closing my speech. (Assent.) Then perhaps
there is this, that certain gentlemen, when they found out that they
had not to fear the law of Fascismo or that of the Government,
which is slower because it is bound to move in accordance with legal
procedure, resumed their bold attitude.

Elimination of the Subversive Elements. The measures adopted to

restore public order are: First of all the elimination of the so-called
subversive elements. There was much clamour after the hauling in
of the nets, but in reality it was only a very small affair. Of two
thousand who were arrested, those who are still in gaol do not reach
the figure of one hundred and fifty. They are in the hands of the
judges. They were elements of disorder and subversion. On the
morrow of each conflict I gave the categorical order to confiscate
the largest possible number of weapons of every sort and kind. This
confiscation, which continues with the utmost energy, has given
satisfactory results. (Assent.) I had to repress every illegal act.

The High Grades of the National Militia. There was another

problem with regard to the National Militia: namely the necessity of
filling the superior posts, to which had to be appointed men coming
from the army with a large personal military experience; this
necessity had to be harmonised with the gratitude due to the small
heads of Fascista “squadrismo,” the body which, by leaving
thousands of glorious dead, had crushed the subversive demagogic
elements.
We have solved this problem. All the ranks of superior officers
above those of “Seniore” have been assigned to the officers coming
from the regular army; all the inferior grades and those of sub-
officers have been given to military men, to “squadristi” who had
previously seen military life.
Moreover, statistics are always worth more than speeches. Ninety-
seven per cent. of the officers of the Militia having a rank superior to
that of “Seniore” come from the officers of the regular army. Out of
about two hundred and thirty officers superior to the rank of
“Seniore,” six are decorated with the Military Order of Savoy, two
with Gold Medals, one hundred and thirty with Silver Medals, eighty
with Bronze Medals.
As this is a day of explanations, even at the risk of abusing your
patience, I must read the list of rewards bestowed on the Chiefs of
the National Militia. General Cesare De Bono, Field Marshal of the
regular army: three Silver Medals, special promotion for war
services, “Croce di Guerra.” General Gandolfo, Field Marshal of the
regular army: two Silver Medals, special promotion for war services.
Hon. Cesare Maria De Vecchi: four Silver Medals, two Bronze Medals,
two “Croci di Guerra.” Italo Balbo: one Silver Medal, one “Croce di
Guerra.” Gustavo Fara, the general well known through all Italy: one
Gold Medal, two Silver Medals, special promotions for war services.
Stringa, Major-General of the regular army: three Silver Medals, one
Bronze Medal, disabled in the war. Ozol Clemente, Major-General in
the regular army: two Silver Medals, “Croce di Guerra.” Ceccherini,
Major-General in the regular army: three Silver Medals, two Bronze
Medals. Zambon, Major-General of the regular army: Silver Medal
and Bronze Medal. Guglielmotti, Major-General of the regular army:
two Silver Medals.
After these follow:
Giuriati, with two Silver Medals; Acerbo, with three Silver Medals
(voices: “Bravo!”); Caradonna, with three Silver Medals; Finzi, with a
Silver Medal and two “Croci di Guerra.”
Not to embarrass the modesty of my friends, I shall not continue
to read the list of these officers of the National Militia,—(Laughter.)—
but this is enough to prove to you that this is a serious institution.
And I add that every day it becomes more so, because I mean that
it shall be so, because all its chiefs mean it.
It might be asked of us: “Why does the Militia remain?” I shall tell
it to you at once: for a very simple reason, to defend Fascismo at
home and also abroad. The word “abroad” might alarm you. Well, I
tell you that abroad there is a difficult atmosphere for Italian
Fascismo. Difficult for the parties of the Right, which, being formed
of national elements, cannot feel enthusiasm for a movement that
exalts our national qualities; difficult for the parties of the Left,
because those elements are our adversaries from the social point of
view, knowing that the Fascista movement is clearly anti-Socialist. It
is well, therefore, that it should be known that there is in Italy a
mighty army of volunteers to defend that special form of political
organisation called Fascismo.
The Militia, moreover, has the object of enabling the army to do its
own work. The army must fight, must get ready for war. It must not
do police work, especially of a political nature, except under
absolutely exceptional circumstances, of which now I do not wish to
think, even hypothetically. As an example I can tell you that last
night, upon my personal instructions, a whole section of Leghorn
was blockaded. Well, one hundred carabineers and three hundred
black shirts sufficed, whilst the army, the official troops, were
sleeping peacefully in their barracks, as was their duty and their
right. Moreover, believe me, so long as in Italy they know that,
besides some tens of thousands of faithful carabineers, there is this
enormous force, attempts at revolt or at sedition will never be dared.

Modifications to the Statute Law. Finally, and this is a manœuvre

of the last few days, have burst forth in Italy the bold defenders of
the Statute, of Liberty and of Parliament. (Laughter.) It seems,
listening to these gentlemen, who had for a long time forgotten the
existence of the Statute, even as a simple historical document,—
(Laughter.)—that the Statute runs a serious risk and that one cannot
even discuss nor examine it.
Well, I think that none of you can consider Camillo Cavour as a
Bolshevist and a Fascista of 1848. Everybody knows that the
Constitutional movement of Piedmont was the work of Cavour.
Everybody knows how the political Constitution was granted. At
Genoa a tumult arose against the Jesuits, believed supporters of
Absolutism. A Commission of Genoese went to Turin and asked for
the expulsion of the Jesuits and the calling out of the Civic Guard.
But Cavour answered: “This is too little, the times are ripe for
something more!” Cavour wrote in his paper, Il Risorgimento: “The
Constitution must be demanded.” And this was promulgated on the
4th of March. In its preamble it says: “The Statute is the
fundamental, perpetual law of the Monarchy.” Four days afterwards
the first Constitutional Ministry of Coalition was formed with the
Moderate Balbo and the Democratic Pareto.
The phrase “The Statute is the fundamental, perpetual and
irrevocable law of the Monarchy” had wounded the ears of the
Democrats. Cavour hastened to interpret it in a relative sense. It is
worth while to listen attentively to this paragraph of Cavour. “How is
it possible,” he said, “how can it be expected that the legislator
would have wished to pledge himself and the nation not to make the
slightest direct change, to bring the smallest improvement to a
political law? But this would mean the removal from the community
of the power of revising the Constitution; it would mean the deprival
of the indispensable power of modifying its political form according
to new social exigencies; this would be such an absurd idea that no
one of those who co-operated in the making of this fundamental law
could conceive it. A nation cannot renounce the power of changing
by legal means its common law.”
After a short time history had to register a first violation of the
Statute, which assumed or presumed that, in order to become a
member of Parliament, it was necessary to be an Italian citizen. On
the 16th of October there was a division between the Right,
amongst which there were the Moderates and the Municipals, and
the Left, to which belonged the Democrats, called the “burnt heads,”
and the Republicans. On the following day these two parties were
agreed in unanimously proclaiming above the Statute that all Italians
could belong to the Subalpine Parliament. The first to benefit by this
violation of the Statute was Alessandro Manzoni; but he declined the
mandate by a letter which represents a fine example of correctness
and political probity. (Approval.)
Nobody, Gentlemen, wishes to overthrow or destroy the Statute,
which rests solidly on firm foundations; but the inhabitants of this
building from 1848 up to to-day have changed. There are other
exigencies, other needs. There is no longer the Piedmontese Italy of
1848! And it is very strange to notice among the defenders of the
Statute those who have violated it in its fundamental laws, those
who have curtailed the prerogatives of the Crown, those who
wanted the Crown to be entirely outside the politics of the nation,
and to become a dead institution. (Loud applause.)

The Abolition of Parliament? They say that this Government does

not like the Chamber of Deputies. (Comments.) They say that we
want to abolish Parliament and deprive it of all its essential
attributes. It is timely to say that the collapse of Parliament is not
desired by me, nor by those who follow my ideas. Parliamentarism
has been severely affected by two phenomena typical of our days:
on one side Syndicalism, on the other Journalism. Syndicalism
gathers by its various organisations all those who have special
interests to protect, who wish to withdraw them from the manifest
incompetence of the political Assembly. Journalism represents the
daily Parliament, the daily platform where men coming from the
Universities, from Science, Industry, from the experience of life itself,
dissect problems with a competence that is very seldom found on
the Parliamentary benches.