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Communication | Special issue | Vol 30, No. 2, 1990, pp.737-740
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S40
Reactions of a Tetrasubstituted Thiocarbonyl Ylide; New Evidence for Two-Step Cycloadditions

Rolf Huisgen* and Grzegorz Mloston

*Institute of Organic Chemistry, University of Munich, Karlstrasse 23, D-80333, München, Germany

Abstract

Zwitterionic intermediates from aliphatic thiocarbonyl yields and tetrasubstituted acceptor olefins can close the 5-membered ring (thiolane) or the 7-membered ring (ketene imine), undergo rotation, and - shown here - furnish cyclopropane and thione in an intramolecular nucleophilic substitution.