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Elemental Sulfur Disproportionation in the Redox Condensation Reaction between o ‐Halonitrobenzenes and Benzylamines
Author(s) -
Nguyen Thanh Binh,
Ermolenko Ludmila,
Retailleau Pascal,
AlMourabit Ali
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201408397
Subject(s) - disproportionation , chemistry , redox , sulfur , benzothiazole , condensation , sulfide , nitro , electron acceptor , inorganic chemistry , condensation reaction , photochemistry , catalysis , organic chemistry , alkyl , physics , thermodynamics
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 .