Mechanism of thiophene formation upon photolysis of enethiol esters

JR Grunwell, DL Foerst, MJ Sanders

Index: Grunwell,J.R. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 7 p. 1142 - 1145

Full Text: HTML

Citation Number: 11

Abstract

Evidence for the mechanism of thiophene formation from the photolysis of enethiol esters was obtained by studying p-monosubstituted vinylthiol acetates. Styrylthiol acetate gave exclusively 3, 4-diphenylthiophene while P-tert-butylvinylthiol acetate yielded P-tert- butylvinyl disulfide and no thiophenes. These results suggest that the photolysis involves homolytic cleavage of the S-acyl bond followed by dimerization of the enethiyl radical at ...