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■ Thio-Claisen Rearrangement of Troponoids

Hitoshi Takeshita, Kingo Uchida, and Hiroaki Mametsuka

*Instituete of Advanced Material Study, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan

Abstract

Several 2-(allylthio)tropones and 2-(propargylthio)tropones gave 2,3-dihydro-(8H)-cyclohepta[b]thiophen-8-ones and (8H)-cyclohepta[b]thiophen-8-ones via a thio-Claisen rearrangement by heating above 180 °C. In cases of γ-substituted allyl derivatives, the results of rearrangement were poor; 2-(prenylthio)tropone gave isoprene by an elimination, similar to 2-(allyloxy)-tropones, while its 3,5,7-trimethyl homolog caused no reaction.