Journal
ORGANIC LETTERS
Volume 12, Issue 24, Pages 5640-5643Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1023807
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Funding
- National Science Foundation [CHE-0910565]
- Donors of the American Chemical Society Petroleum Research Funds [50086-URI]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0910565] Funding Source: National Science Foundation
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A facile and operationally convenient catalytic procedure for oxidative cleavage of alkenes is described. In situ formed [hydroxy(4-carboxyphenyl)iodonium]ion, 2, from the oxidation of 4-iodobenzoic acid, 1, has been shown to facilitate the cleavage of a variety of alkenes in presence of Ozone as a co-oxidant. Optimization of the reaction conditions using 1-phenyl-1-cyclohexene, 3, and the competitive oxidative cleavage of different substrates using the optimized conditions has uncovered important mechanistic details of the reaction.
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