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Communication | Regular issue | Vol 29, No. 11, 1989, pp.2069-2074
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5165
A Stable Seven-membered Ring Ketene Imine from a Thiocarbonyl Ylide and an Acceptor Olefin

Rolf Huisgen,* Elke Langhals, Grzegorz Mloston, and Takumi Ohshima

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

Abstract

2,2,4,4-Tetramethyl-3-thioxocyclobutanone S-methylide (2), generated from the 1,3,4-thiadiazoline 1 by N2 extrusion, combines with trans- and cis-1,2-dicyano-1,2-bis(trifluoromethyl)ethylene (7) furnishing nonstereospecifically five-membered thiolanes (8, 16) and a strained cyclic ketene imine in parallel reactions. The results of a mechanistic study are interpreted by zwitterionic intermediates.