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Communication | Regular issue | Vol 75, No. 10, 2008, pp.2415-2420
Published online, 26th May, 2008
DOI: 10.3987/COM-08-11412
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


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.