title: Elemental sulfur disproportionation in the redox condensation reaction between o-halonitrobenzenes and benzylamines.
abstract: The disproportionation of elemental sulfur at moderate temperatures is investigated in the redox condensation involving o-halonitrobenzenes 1 and benzylamines 2. As a redox moderator, elemental sulfur plays the dual role of both electron donor and acceptor, generating its lowest and highest oxidation states: S(-2) (sulfide equivalent) in benzothiazole 3 and S(+6) (sulfate equivalent) in sulfamate 4, and filling the electron gap of the global redox condensation process. Along with this process, a cascade of reactions of reduction of the nitro group of 1, oxidation of the aminomethyl group of 2, metal-free aromatic halogen substitution, and condensation finally led to 2-arylbenzothiazoles 3.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France). nguyen@icsn.cnrs-gif.fr.
authors.forename: Thanh Binh
authors.initials: TB
authors.lastname: Nguyen
authors.forename: Ludmila
authors.initials: L
authors.lastname: Ermolenko
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Ali
authors.initials: A
authors.lastname: Al-Mourabit
keywords: benzothiazoles; multicomponent reactions; redox condensation; sulfur; sulfur disproportionation