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Communication | Regular issue | Vol 22, No. 5, 1984, pp.1053-1056
Published online, 1st January, 1970
DOI: 10.3987/R-1984-05-1053
Benzyne-induced Fragmentation Reactions of 1,3-Dithiolanes

Juzo Nakayama,* Hiroshi Ozasa, and Masamatsu Hoshino

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

Abstract

2-Monosubstituted 1,3-dithiolanes, on reaction with benzyne, undergo two types of fragmentation, one of which gives phenyl vinyl sulfide and thioaldehydes (corresponding aldehydes as the final products) and the other gives phenyl dithiocarboxylates and ethylene. Meanwhile, 2,2-disubstituted 1,3-dithiolanes undergo the sole fragmentation yielding phenyl vinyl sulfide and thioketones.