title: New catalytic system for aminohalogenation of beta-methyl-beta-nitrostyrenes to give opposite regiochemistry.
abstract: 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-TsNCl(2)). The reaction was achieved by using MnSO(4) 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.
authors.affiliation: School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, PR China.
authors.forename: San-Jun
authors.initials: SJ
authors.lastname: Zhi
authors.forename: Hao
authors.initials: H
authors.lastname: Sun
authors.forename: Guangqian
authors.initials: G
authors.lastname: Zhang
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
authors.forename: Yi
authors.initials: Y
authors.lastname: Pan