Trimethylsilyl chloride promoted synthesis of α-branched amines by nucleophilic addition of organozinc halides to nitrones.

A general procedure for the nucleophilic addition of organozinc halides with nitrones in the presence of trimethylsilyl chloride has been developed. Trimethylsilyl chloride was found to be both an indispensable reaction promoter and a ready hydroxylamine protective agent in these reactions. The produced O-(trimethylsilyl)hydroxylamines can be easily reduced into corresponding amines just by a zinc-copper couple in saturated aqueous NH(4)Cl solution.

(Z)-N-(2-Chloro-benzyl-idene)aniline N-oxide.

In the title compound, C(13)H(10)ClNO, the central C-N bond has considerable double-bond character and the N-O bond indicates a formal negative charge on the O atom. The mol-ecule is stabilized by an intra-molecular C-H⋯O hydrogen bond. The geometry about the C=N bond is Z [C-C-N-O torsion angle = -4.