New catalytic system for aminohalogenation of β-methyl-β-nitrostyrenes to give opposite regiochemistry?

Organic & Biomolecular Chemistry Pub Date: 2009-12-07 DOI: 10.1039/B914944A

Abstract

A new combination of catalyst and co-additive has been found for aminohalogenation reaction of β-methyl-β-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.

Graphical abstract: New catalytic system for aminohalogenation of β-methyl-β-nitrostyrenes to give opposite regiochemistry
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