Rearrangement of beta-chloro N-oxides to hydroxylamines: opening of the oxazetidinium intermediate by different nucleophiles.
The rearrangement of beta-chloro N-oxides to hydroxylamines is stereospecific in accord with the presence of a cyclic oxazetidinium intermediate. The latter opens with a range of nucleophiles (carboxylates, cyanide, azide, and thiols).
Wefelscheid
Ulrike K
UK
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, United Kingdom.
Woodward
Simon
S
D019811:Hydroxylamine / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D010087:Oxides; D019811:Hydroxylamine