Additional of functional vinylzinc reagents to nitrones: synthesis of (E)-N-allylhydroxylamines and their rearrangement into (E)-O-allylhydroxylamines.

The vinylzinc reagents derived from hydrozirconation of alkynes and transmetallation add readily to nitrones to yield pure (E)-N-allylhydroxylamines; some of these rearrange into O-allylhydroxylamines.

(1S)-(Z)-2-benzyloxy-N-(3-methyl-1-butylidene)-1-phenylethylamine N-oxide.

The preparation and crystal structure of the title compound, C(20)H(25)NO(2), are described. The N atom substituent of the nitrone function adopts a conformation which minimizes the 1,3-allylic strain.