Chloration et S-oxydation du benzo[b]thiophène par l'hypochlorite de tertiobutyle. Mécanisme de la réaction

In the reaction with benzothiophene, t-butyl hypochlorite acts simultaneously as a smooth oxidizing agent and as a chlorinating agent since it is a source of both hypochlorous acid and chlorine. The mixture of all the products obtained imply that the reaction intermediate is the unstable benzothiophene I-oxide which was shown to be present by the stop flow technique. The chlorine formed traps the highly reactive benzothiophene 1-oxide in situ to give the observed products.