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Communication | Regular issue | Vol 23, No. 9, 1985, pp.2207-2212
Published online, 1st January, 1970
DOI: 10.3987/R-1985-09-2207
1,3-Cycloadditions of 2,2,4,4-Tetramethylcyclobutane-1-one-3-thione S-Methylide

Rolf Huisgen,* Grzegorz Mloston, and Claudia Fulka

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


The 1,3,4-thiadiazoline 2, prepared from 2,2,4,4-tetramethylcyclobutane-1-one-3-thione and diazomethane, loses N2 at 40°C; the thiocarbonyl ylide 5 is a transient intermediate which in situ undergoes 1,3-dipolar cycloadditions to electron-deficient dipolarophiles with C=C, C=C, C=S, C=O, and N=N bonds. Structures and mechanism are discussed.