Synthesis and Ring Expansion of Vinylazetidines. A Synthesis of Hydroazocines

Alfred Hassner, Norbert Wiegand

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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 languageEnglish
Pages (from-to)3652-3656
Number of pages5
JournalJournal of Organic Chemistry
Issue number19
StatePublished - 1986


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