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Report | Regular issue | Vol 23, No. 2, 1985, pp.325-330
Published online, 1st January, 1970
DOI: 10.3987/R-1985-02-0325
The Trapping of Sulfenic Acids from Penicillin Sulfoxides. Heterocyclic Mercaptans

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

*Faculty of Pharmacy , University of Alberta, Edmonton, Alberta T6G, 2N8, Canada


Various heterocyclic thiols have been used for trapping the azetidinone sulfenic acids obtained by the thermolysis of penicillin sulfoxides. The ester function was found to be important in determining the unsym-azetidinone disulfide (α,β- or β,γ-unsaturated) isomer formed. All β,γ-isomers prepared reacted with cupric chloride to give the 2-chloromethylpenams.