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Report | Regular issue | Vol 23, No. 6, 1985, pp.1403-1409
Published online, 1st January, 1970
DOI: 10.3987/R-1985-06-1403
The Trapping of Sulfenic Acids from Penicillin Sulfoxides. Aryl Mercaptans

Ronald G. Micetich,* Samarendra N. Maiti, Motoaki Tanaka, Tomio Yamazaki, and Kazuo Ogawa

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

Abstract

Aryl mercaptans, unlike heterocyclic mercaptans, reacted exceptionally slowly with penicillin sulfoxides. These reactions are affected by the substituent at the C-6 position of the penam, and by the nature of the ester group at the C-3 position. The unsym-azetidinone disulfides obtained from these reactions, unlike those from heterocyclic mercaptans, did not react with halogenating agents such as cupric chloride.