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Paper | Special issue | Vol 90, No. 1, 2015, pp.529-539
Published online, 6th August, 2014
DOI: 10.3987/COM-14-S(K)56
Thermal [2+2]-Cycloadditions of Diphenylketene with Aryl- and Hetaryl-Substituted Thioketones

Grzegorz Mlostoń,* Katarzyna Urbaniak, Anna Szychowska, Anthony Linden, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Abstract

The reaction of diphenylketene (1) with aryl- and hetaryl-substituted thioketones (2) gave the corresponding 3,3,4,4-tetraarylthietan-2-ones (3) in good yields. Remarkably, the reactions with bis-hetaryl-substituted thioketones occurred significantly faster compared with those involving the bis-aryl-substituted thioketones. The structure of compound 3c has been established by X-ray crystallography.