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Pure Appl. Chem., 2000, Vol. 72, No. 12, pp. 2259-2264

Mechanisms and consequences of oxygen transfer reactions

Peter Beak*, David R. Anderson, Stephen G. Jarboe, Mitchell L. Kurtzweil and Keith W. Woods

Abstract: The geometry about oxygen in the transition-state structures for oxygen transfers from a nitrone to phosphorous, from a percarboxylic acid to a carbon­carbon double bond, and from an N-sulfonyl oxaziridine to a carbon­carbon double bond have been evaluated by the endocyclic restriction test. The former can proceed at an oblique angle, while the latter two require a large angle between the entering and leaving groups on oxygen. This information is used to determine the mechanism of the aldehyde-dependent oxygen transfer from molecular oxygen to a carbon­carbon double bond.