The Journal of Organic Chemistry

Small rings. 29. Synthesis and ring expansion of vinylazetidines. A synthesis of hydroazocines

A Hassner, N Wiegand

Index: Hassner, Alfred; Wiegand, Norbert Journal of Organic Chemistry, 1986 , vol. 51, # 19 p. 3652 - 3656

Full Text: HTML

Citation Number: 28

Abstract

A synthesis of 2-vinylazetidines 1 la-c by means of CISOzNCO addition to 1, 3-dienes followed by AlH, reduction is described. One example (1 la) 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).