期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 50, 页码 13808-13812出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408397
关键词
benzothiazoles; sulfur; multicomponent reactions; redox condensation; sulfur disproportionation
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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