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Communication | Regular issue | Vol 23, No. 8, 1985, pp.1907-1910
Published online, 1st January, 1970
DOI: 10.3987/R-1985-08-1907
Regiochemistry of Thermal Extrusion of Sulfur from 2,6-Diaryl-1,4-dithiins Yielding 2,5- and 3,4-Diarylthiophenes

Juzo Nakayama,* Masahiro Shimomura, Michiko Iwamoto, and Masamatsu Hoshino

*Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan


The predominant formation of 2,5-diarylthiophenes over the 3,4-diaryl isomers by thermolyses of a series of 2,6-diaryl-1,4-dithiins 3,4-diaryl supports that this sulfur extrusion reaction proceeds by the mechanism involving the valence isomerization to thiocarbonyl ylide intermediate possessing a thiirane structure in the rate-determining step.