title: Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds.
abstract: N-Alkyl-N-chlorosulfonamides add to alkenes under copper(I) catalysis. In reactions of styrene derivatives with terminal double bonds the addition products were obtained in excellent yield and high regioselectivity. Lower yields are obtained in addition reactions to non-aromatic alkenes. The reaction most likely proceeds via a redox catalysis and amidyl radicals, a concerted mechanism has been ruled out and a polar mechanism via chloronium ions would lead to the opposite regiochemistry.
authors.affiliation: Organisch-Chemisches Institut, WWU Münster, Corrensstraße 40, 48149 Münster, Germany.
authors.forename: Gerold
authors.initials: G
authors.lastname: Heuger
authors.affiliation: Organisch-Chemisches Institut, WWU Münster, Corrensstraße 40, 48149 Münster, Germany ; Institut für Organische Chemie, Justus-Liebig-Universität Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany.
authors.forename: Richard
authors.initials: R
authors.lastname: Göttlich
keywords: N-chlorosulfonamides; addition reactions; catalysis; haloamination; radical reaction