Reaction of diarylcarbinols and diarylolefins with thionyl chloride: A synthesis of 3-arylbenzothiophens

Abstract

Treatment of 1,l-diphenylalkan-1-ols and 1,l-diphenylalk-l-enes with thionyl chloride gives 3-phenyl-benzo[b]thiophens in approximately 50% yields. Also formed in these reactions are 2-chloro-1,l- diphenylalk-l-enes and 1,2-dichloro-1,l-diphenylalkanes. 5,6-Dihydrobenzo[b]naphtho[l,2-dlthiophen was formed from l-phenyl-3,4-dihydronaphthalene under these conditions.