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Updated: Apr 22, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Elemental sulfur disproportionation in the redox condensation reaction between o-halonitrobenzenes and benzylamines
Thanh Binh Nguyen1, Ludmila Ermolenko, Pascal Retailleau
1Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France). nguyen@icsn.cnrs-gif.fr.
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.
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