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Communication | Regular issue | Vol 29, No. 11, 1989, pp.2075-2078
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5166
Ring Contraction of a Cyclic Seven-membered Ketene Imine

Rolf Huisgen,* Elke Langhals, and Takumi Ohshima

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


A cyclic ketene imine prepared from 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-methylide and 2,3-bis(trifluoromethyl) fumaronitrile rearranges to the isomeric thiolane. The high dependence of the rate on solvent polarity and the steric course are in accordance with an open-chain zwitterionic intermediate.