title: Regioselective Synthesis of Mixed Indole 2,3-Bis(sulfides). A Study of the Mechanism of the Second Sulfenylation of Indole.
abstract: Sulfenylation of indole using sulfenyl chlorides leads to the initial formation of a 3-indolyl sulfide, while excess reagent introduces a second sulfide at the 2-position of the ring. The mechanism of this second sulfenylation has not, to date, been rigorously elucidated. The development of the first, regioselective synthesis of mixed indole 2,3-bis(sulfides) has allowed the study of the sulfenylation of 3-indolyl sulfides using a different sulfenyl chloride. Our results afford evidence that the reaction proceeds via an intermediate 3,3-disulfenylated indolenine species, with subsequent migration of one of the sulfide groups to the 2-position.
authors.affiliation: Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe-Claire-Dorval, Québec, H9R 4P8 Canada.
authors.forename: Pierre
authors.initials: P
authors.lastname: Hamel
authors.forename: Patrice
authors.initials: P
authors.lastname: Préville