Experimental investigation into the mechanism of the epoxidation of aldehydes with sulfur ylides |
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| Authors: | Edwards David R Montoya-Peleaz Pedro Crudden Cathleen M |
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| Affiliation: | Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, ON, Canada K7M 3N6. cruddenc@chem.queensu.ca |
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| Abstract: | 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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