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■ New Thiocarbonyl Ylides from Thiobenzophenone

Rolf Huisgen and Li Xingya

*Institut für Organische Chemie, Universität München, Karlstrasse 23, D-80333 München, Germany

Abstract

Thiobenzophenone is converted to 1,3,4-thiadiazolines by reaction with diazoethane, phenyldiazomethane or diphenyldiazomethane at -78 °C. Extrusion of nitrogen from the thiadiazolines furnishes thiocarbonyl ylides which, in turn, undergo electrocyclic ring closure to form thiiranes. Thiobenzophenone S-ethylide and S-benzylide can be intercepted by suitable dipolarophiles to provide 5-membered 1,3-cycloadducts.