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Report | Regular issue | Vol 22, No. 12, 1984, pp.2757-2763
Published online, 1st January, 1970
DOI: 10.3987/R-1984-12-2757
■ The Chlorinolysis of Azetidinone Disulfides

Ronald G. Micetich,* Rajeshwar Singh, Werner O. Merlo, Daniel M. Tetteh, Chia-Cheng Shaw, and Robert B. Morin

*Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Abstract

The chlorinolysis of dithiazeneazetidinones, unsym-azetidinone disulfides, and 2-chloromethylpenams, with sulfuryl chloride produce the 2-[2’(R and S)-chloro-4’-oxoazetidin-1’-yl]-3-chloromethyl-3-chlorosulfenylbutyric acid ester isomers in which the S-isomer predominates. Treatment of this compound (R and S isomers) with pyridine results in elimination of HSCl and formation of the Z and E isomers in which the Z isomer predominates.