TY - JOUR
T1 - Synthesis and Ring Expansion of Vinylazetidines. A Synthesis of Hydroazocines
AU - Hassner, Alfred
AU - Wiegand, Norbert
PY - 1986
Y1 - 1986
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).
UR - http://www.scopus.com/inward/record.url?scp=33845376457&partnerID=8YFLogxK
U2 - 10.1021/jo00369a018
DO - 10.1021/jo00369a018
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AN - SCOPUS:33845376457
SN - 0022-3263
VL - 51
SP - 3652
EP - 3656
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -