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Burgess Reagent Facilitated Alcohol Oxidations in DMSO

Prakash R. Sultane and Christopher W. Bielawski*

*Institute for Basic Science (IBS) & Ulsan National Institute of Science and Technology (UNIST), Ulsan 44919, Republic of Korea, Email: bielawskiunist.ac.kr

P. R. Sultane, C. W. Bielawski, J. Org. Chem., 2017, 82, 1046-1052.

DOI: 10.1021/acs.joc.6b02629 (free Supporting Information)


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Abstract

In the presence of dimethyl sulfoxide, the Burgess reagent efficiently and rapidly facilitates the oxidation of a broad range of primary and secondary alcohols to their corresponding aldehydes and ketones in excellent yields and under mild conditions. This oxidation can be combined with Wittig olefinations. A mechanism similar to those described for the Pfitzner-Moffatt and Swern oxidations is proposed.

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proposed mechanism



Key Words

Burgess reagent, DMSO, aldehydes, ketones


ID: J42-Y2017