A mechanistic study of the epoxidation of aldehydes with sulfur ylides has been carried out. The DeltaG++ of the reaction was determined to be 22.2 kcal/mol at 298 K. A 13C kinetic isotope effect was determined to be 1.026 for the carbonyl carbon of benzaldehyde. A secondary deuterium isotope effect was determined to be 0.93 for the aldehydic hydrogen atom of benzaldehyde. Substituent effects on reaction rate were studied, and a Hammett rho of +2.50 was found.
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| http://dx.doi.org/10.1021/ol702300d | DOI Listing |
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