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Paper | Special issue | Vol 93, No. 1, 2016, pp.127-139
Published online, 6th October, 2015
DOI: 10.3987/COM-15-S(T)8
New Applications of Hetaryl Thioketones for the Synthesis of Hetaryl-Substituted Ethenes via ‘Two-Fold Extrusion Reaction’

Grzegorz Mlostoń, Katarzyna Urbaniak, Aneta Pawlak, and Heinz Heimgartner*

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


A series of aryl/hetaryl thioketones was applied for the reactions with aryl/hetaryldiazomethanes yielding, after elimination of N2, the corresponding thiiranes. The relatively unstable dihetaryldiazomethanes were generated in situ from the corresponding hydrazones by oxidation with DMSO. The obtained thiiranes were converted into tetraaryl/hetaryl-substituted ethenes in good yields by desulfurization performed with tris(diethylamino)phosphine ((Et2N)3P).