Synthesis and Ring Expansion of Vinylazetidines. A Synthesis of Hydroazocines

Alfred Hassner; Norbert Wiegand

doi:10.1021/jo00369a018

Synthesis and Ring Expansion of Vinylazetidines. A Synthesis of Hydroazocines

Alfred Hassner
, Norbert Wiegand

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A synthesis of 2-vinylazetidines 11a-c by means of ClSO₂NCO addition to 1,3-dienes followed by A1H₃ reduction is described. One example (11a) underwent Michael additions with several olefinic and acetylenic substrates. The 1,2-divinylazetidines obtained with the latter reagents underwent Cope rearrangements when heated and gave rise to tautomeric mixtures of 3,4,7,8- and 1,4,7,8-tetrahydroazocines (21 and 22).

Original language	English
Pages (from-to)	3652-3656
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	51
Issue number	19
DOIs	https://doi.org/10.1021/jo00369a018
State	Published - 1986

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abstract = "A synthesis of 2-vinylazetidines 11a-c by means of ClSO2NCO addition to 1,3-dienes followed by A1H3 reduction is described. One example (11a) underwent Michael additions with several olefinic and acetylenic substrates. The 1,2-divinylazetidines obtained with the latter reagents underwent Cope rearrangements when heated and gave rise to tautomeric mixtures of 3,4,7,8- and 1,4,7,8-tetrahydroazocines (21 and 22).",

author = "Alfred Hassner and Norbert Wiegand",

year = "1986",

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journal = "Journal of Organic Chemistry",

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AU - Wiegand, Norbert

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N2 - A synthesis of 2-vinylazetidines 11a-c by means of ClSO2NCO addition to 1,3-dienes followed by A1H3 reduction is described. One example (11a) underwent Michael additions with several olefinic and acetylenic substrates. The 1,2-divinylazetidines obtained with the latter reagents underwent Cope rearrangements when heated and gave rise to tautomeric mixtures of 3,4,7,8- and 1,4,7,8-tetrahydroazocines (21 and 22).

AB - A synthesis of 2-vinylazetidines 11a-c by means of ClSO2NCO addition to 1,3-dienes followed by A1H3 reduction is described. One example (11a) underwent Michael additions with several olefinic and acetylenic substrates. The 1,2-divinylazetidines obtained with the latter reagents underwent Cope rearrangements when heated and gave rise to tautomeric mixtures of 3,4,7,8- and 1,4,7,8-tetrahydroazocines (21 and 22).

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Synthesis and Ring Expansion of Vinylazetidines. A Synthesis of Hydroazocines

Abstract

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