Catalytic aminohalogenation reaction of b-nitrostyrenes with N,N-dichloro-4-toluenesulfonamide resulting in dichlorinated halo amides with opposite regiochemistry to previous systems.

[摘要]：Derivatives, and Condensed Benzenoid Compounds) Section The reaction of b-nitrostyrenes with N,N-dichloro-4-toluenesulfonamide (TsNCl2) was successfully conducted by using either CuCl or 4-(dimethylamino)pyridine (DMAP) as the catalyst. The reaction resulted in dichloro amine products with opposite regiochem. to that previously obsd. In the presence of DMAP, the reaction proceeded smoothly to completion within 24 h at room temp. and gave good chem. yields (65-88%). The structure of 2,2-dichloro-2-nitro-1-(4-toluenesulfonamido)-1-(4-methylphenyl)ethane was confirmed by x-ray crystal structure anal. [orthorhombic, space group Pbca, a 7.748(5), b 19.85(1), c 23.03(1) ? V 3542(3) ?, Z 8]. This reaction is proposed to occur through a new mechanism involving a chloronium intermediate.

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