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BY-NC-ND 3.0 license Open Access Published by De Gruyter June 2, 2014

Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXV [1]. 1-Alkoxy-2-alkyl-2 H-isoindole — o-chinoide Hetarene mit unsymmetrischer Struktur / Studies on the Chemistry of Isoindoles and Isoindolenines, XXXV [1]. 1-Alkoxy-2-alkyl-2H-isoindoles — o-Quinonoid Hetarenes with Unsymmetric Structure

  • Richard P. Kreher , Hans Hennige , Frank Jelitto and Johannes Preut
From the journal Zeitschrift für Naturforschung B
https://doi.org/10.1515/znb-1989-0923
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3-Alkoxy-2-methyl-1 H-isoindolium salts have been prepared either via regioselective O-alkylation of the corresponding 2-alkyl-isoindoline-1-ones or via regioselective N-alkylation of 3-alkoxy-1 H-isoindoles with trialkyloxonium tetrafluoroborates or with alkyl trifluoromethanesulfonates. Deprotonation of these stable precursors leads to the generation of reactive 1-alkoxy-2-alkyl-2H-isoindoles in solution. Reactions with CC-dienophiles (N-substituted maleic imides) give rise to the formation of 1 : 2-adducts. The two step reaction comprises Michael-addition and Diels-Alderaddition; the isolation of an initially formed 1:1-adduct is possible in the case of steric hindrance. Constitution and configuration of a representative 1 : 2-adduct has been established by X-ray crystal structure determination.

Keywords : 1-Alkoxy-2-alkyl-2 H-isoindoles; Generation and Characterization; Addition and Cycloaddition Reactions with CC-Dienophiles
Received: 1989-5-11
Published Online: 2014-6-2
Published in Print: 1989-9-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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From the journal
Zeitschrift für Naturforschung B
Zeitschrift für Naturforschung B
Volume 44 Issue 9

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