Investigating the reaction of N-carbobenzoxy-O-carbobenzoxy- hydroxylamine with dimethyl sulfoxide: formation of S,S-dimethyl-N-[(phenylmethoxy)- carbonyl]sulfoximine.
[Reaction: see text]. N-carbobenzoxy-O-carbobenzoxyhydroxylamine (1a) underwent a thermally induced reaction in DMSO in which there is net N-alpha-eliminative oxidation with tandem oxidative incorporation of DMSO to yield S,S-dimethyl-N-[(phenylmethoxy)carbonyl]sulfoximine. Mechanisms for the formation of the sulfoximine are presented as well as the product characterizations, including the X-ray crystal structure.
Darbeau
Ron W
RW
Department of Chemistry, McNeese State University, Lake Charles, Louisiana 70609, USA. rdarbeau@mail.mcneese.edu
Alvarez
Noe T
NT
Trahan
Gregory A
GA
Fronczek
Frank R
FR