S. Sakanoue, Shinya Harasawa, N. Yamazaki
Nov 25, 1990
Citations
0
Influential Citations
11
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
Pyrolysis of O-2-(1-benzyl-2-pyrrolidinyl and 2-piperidyl)ethyl O-phenyl thionocarbonates (4 and 25) in acetonitrile gave 1-benzyl-4-phenoxyhexahydro-1H-azepine (7) and 1-benzyl-4-phenoxyoctahydroazocine (26) with liberation of COS in 55% and 32% yields, accompanied with 2-(2-phenoxyethyl)pyrrolidine and piperidine (8 and 27), via the azetidinum intermediate (6). On the other hand, O-phenyl O-2-(2-tetrahydrothienyl)ethyl thionocarbonate (32) resulted in the predominant formation of the O, S-rearrangement product (35) in 53% yield.