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Published October 19, 2005 | public
Journal Article Open

Enhancing 2-Iodoxybenzoic Acid Reactivity by Exploiting a Hypervalent Twist


A rearrangement of hypervalent bonds, or twisting, proves to be the rate-determining step in the 2-iodoxybenzoic acid (IBX) oxidation of alcohols. From this insight, derived from density functional theory calculations, we explain why IBX oxidizes large alcohols faster than small ones and propose a modification to the reagent predicted to make it more active.

Additional Information

© 2005 American Chemical Society. Received July 5, 2005. Publication Date (Web): September 15, 2005. We thank the NSF (predoctoral fellowship to J.T.S. and CTS-0132002) and the DOE (DE-PS36-03GO93015) for financial support. We thank Prof. Brian M. Stoltz and Dr. Jonas Oxgaard for useful discussions concerning the mechanism of the reaction and constrained alcohol−IBX complexes.

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Supplemental Material - ja054446xsi20050824_011746.pdf


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August 19, 2023
August 19, 2023