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■ Synthesis and Properties of S-Aminothiiranium Salts of anti- and syn-9,9’-Bibenzonorbornenylidenes and 2,2’-Biadamantylidene

Yoshiaki Sugihara,* Rie Ohtsu, and Juzo Nakayama*

*Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Shimo-okubo, Sakura-ku, Saitama 338-8570, Japan

Abstract

S-Aminothiiranium salts 5a-c of anti- and syn-9,9’-bibenzo- norbornenylidenes and 2,2’-biadamantylidene were synthesized by reacting thiiranes 3a-c with O-mesitylenesulfonylhydroxylamine. Decomposition of 5a and 5c in CD₂Cl₂ at rt yielded a mixture of the corresponding alkenes and thiiranes, whereas that of 5b yielded 1,2-thiazetidin-2-ium salts 8b. A CH₂Cl₂ solution of 8b was treated briefly with aq. NaHCO₃ at 0 °C to produce N-unsubstituted 1,2-thiazetidine10b.