New catalytic system for aminohalogenation of beta-methyl-beta-nitrostyrenes to give opposite regiochemistry.
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.
Zhi
San-Jun
SJ
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, PR China.
Sun
Hao
H
Zhang
Guangqian
G
Li
Guigen
G
Pan
Yi
Y