58042-64-1Relevant articles and documents
Reactions of Halothiophenes with Arene- and Hetarenethiols
Deryagina,Papernaya,Klyba,Voronkov
, p. 1296 - 1298 (2007/10/03)
Reactions of halothiophenes with sulfanyl radicals generated from arene- and hetarenethiols at 140-200°C have been studied for the first time. The reactions result in replacement of halogen in 2-bromothiophene and 2,5-dichloro-, 2-bromo-5-chloro-, and 2,5-dibromothiophenes. The two halogen atoms in dihalothiophenes are replaced only by phenylthio radical generated from benzenethiol. 4-Methylbenzenethiol and naphthalene-1-thiol react with halothiophenes most selectively, yielding corresponding unsymmetrical sulfides. The reactions with 2-thiophenethiol are accompanied by self-condensation to give dithienyl sulfide. The reactions of arene- and hetarenethiols with halothiophenes provide a synthetic route to unsymmetrical sulfides of the thiophene series, which are difficult to obtain by other methods, and allow prediction of the behavior of other sulfanyl radicals in similar reactions.