Enhancing 2-Iodoxybenzoic Acid Reactivity by Exploiting a Hypervalent Twist

Su, Julius T. and Goddard, William A., III (2005) Enhancing 2-Iodoxybenzoic Acid Reactivity by Exploiting a Hypervalent Twist. Journal of the American Chemical Society, 127 (41). pp. 14146-14147. ISSN 0002-7863. doi:10.1021/ja054446x. https://resolver.caltech.edu/CaltechAUTHORS:20170420-132741288

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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.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja054446x	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ja054446x	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/ja054446x	Publisher	Supporting Information

ORCID:

Author	ORCID
Goddard, William A., III	0000-0003-0097-5716

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.

Funders:

Funding Agency	Grant Number
NSF Predoctoral Fellowship	UNSPECIFIED
Department of Energy (DOE)	DE-PS36-03GO93015

Issue or Number:

DOI:

10.1021/ja054446x

Record Number:

CaltechAUTHORS:20170420-132741288

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20170420-132741288

Official Citation:

Enhancing 2-Iodoxybenzoic Acid Reactivity by Exploiting a Hypervalent Twist Julius T. Su and William A. Goddard III Journal of the American Chemical Society 2005 127 (41), 14146-14147 DOI: 10.1021/ja054446x

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ID Code:

76780

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

20 Apr 2017 20:36

Last Modified:

15 Nov 2021 17:02

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