Published October 19, 2005
| Version Supplemental Material
Journal Article
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Enhancing 2-Iodoxybenzoic Acid Reactivity by Exploiting a Hypervalent Twist
Abstract
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.Attached Files
Supplemental Material - ja054446xsi20050824_011746.pdf
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Additional details
Identifiers
- Eprint ID
- 76780
- DOI
- 10.1021/ja054446x
- Resolver ID
- CaltechAUTHORS:20170420-132741288
Funding
- NSF Predoctoral Fellowship
- Department of Energy (DOE)
- DE-PS36-03GO93015
Dates
- Created
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2017-04-20Created from EPrint's datestamp field
- Updated
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2021-11-15Created from EPrint's last_modified field