Mechanisms and consequences of oxygen transfer reactions*
Peter Beak**, David R. Anderson, Stephen G. Jarboe, Mitchell L. Kurtzweil,
and Keith W. Woods
Department of Chemistry, University of Illinois at
Urbana-Champaign, Urbana, IL 61801, USA
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.
*Plenary lecture presented at the 15th
International Conference on Physical Organic Chemistry (ICPOC 15), Göteborg,
Sweden, 8 –13 July 2000. Other presentations are published in this
issue, pp. 2219 –2358.
**Corresponding author
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