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Keywords = 3-benzyloxy-1-butenes

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6 pages, 981 KiB  
Short Note
(S,Z)-1,4-Bis(benzyloxy)hexa-3,5-dien-2-ol
by Akihiro Iyoshi, Yo Miyazaki, Masakazu Tanaka and Atsushi Ueda
Molbank 2024, 2024(3), M1848; https://doi.org/10.3390/M1848 - 10 Jul 2024
Viewed by 366
Abstract
Naturally occurring carbohydrates serve as useful building blocks, and various derivatives have been employed in natural product syntheses. For instance, some aldoses can be converted to 1,3-dienes via the Wittig reaction at the anomeric carbon, accompanied by the E2 elimination of the C3-alkoxy [...] Read more.
Naturally occurring carbohydrates serve as useful building blocks, and various derivatives have been employed in natural product syntheses. For instance, some aldoses can be converted to 1,3-dienes via the Wittig reaction at the anomeric carbon, accompanied by the E2 elimination of the C3-alkoxy group. However, there are few examples of terminal 1,3-diene synthesis. We report the synthesis of (S,Z)-1,4-bis(benzyloxy)hexa-3,5-dien-2-ol, featuring a terminal 1,3-diene and chiral secondary alcohol, derived from 2,3,5-tri-O-benzyl-d-arabinofuranose with methyltriphenylphosphonium bromide and potassium tert-butoxide in a single step. The synthesized terminal 1,3-diene demonstrated effective reactivity in a cross-metathesis reaction with cis-1,4-diacetoxy-2-butene. Full article
(This article belongs to the Section Organic Synthesis)
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174 KiB  
Article
Gas-Phase Pyrolytic Reaction of 4-Aryl-3-buten-2-ols and Allyl Benzyl Ethers: Kinetic and Mechanistic Study
by Alya M. Al-Etaibi, Nouria A. Al-Awadi, Maher R. Ibrahim and Yehia A. Ibrahim
Molecules 2010, 15(1), 407-419; https://doi.org/10.3390/molecules15010407 - 20 Jan 2010
Cited by 2 | Viewed by 13654
Abstract
Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH3)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, p-NO2 [...] Read more.
Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CH-CH(CH3)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, p-NO2) and 7-X-1,2-dihydronaphthalene derivatives (where X is H, MeO); FVP of 1-aryl-3-benzyloxy1-1-butenes and benzyl cinnamyl ethers [ArCH=CHCH(X)OCH2Ph, where Ar is phenyl, p-MeO, p-Me, p-Cl, X is H, Me, Ph] gave the corresponding but-2-en-1-ylbenzene derivatives (ArCH2CH=CH-X, where X is H, Me, Ph) together with benzaldehyde. The proposed mechanism of these pyrolytic transformations was supported by kinetic and product analysis. Full article
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