title: Rearrangement of beta-chloro N-oxides to hydroxylamines: opening of the oxazetidinium intermediate by different nucleophiles.
abstract: 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).
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, United Kingdom.
authors.forename: Ulrike K
authors.initials: UK
authors.lastname: Wefelscheid
authors.forename: Simon
authors.initials: S
authors.lastname: Woodward
mesh_terms: D019811:Hydroxylamine / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D010087:Oxides; D019811:Hydroxylamine