Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 3, Pages 628-631Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b914944a
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Funding
- National Natural Science Foundation of China [2077056]
- Robert Welch Foundation [D-1361]
- Qing-Lan Program of Jiangsu Province
- Education Ministry of China
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A new combination of catalyst and co-additive has been found for aminohalogenation reaction of beta-methyl-beta-nitrostyrenes with N,N-dichloro-p-tolunesulfonamide (4-TsNCl2). The reaction was achieved by using MnSO4 as the catalyst together with tolunesulfonamide to give vicinal haloamino nitroalkanes with opposite regiochemistry to that generated from other electron-deficient olefins observed previously. The reaction proceeded smoothly at room temperature under nitrogen atmosphere to give useful to good yields and excellent regio and stereoselectivity. A mechanism involving the formation of chloronium intermediate was proposed to explain the resulting regio and stereochemistry.
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