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Burgess Reagent Facilitated Alcohol Oxidations in DMSO

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Title
Burgess Reagent Facilitated Alcohol Oxidations in DMSO
Author(s)
Prakash R. Sultane; Christopher W. Bielawski
Subject
STEREOSELECTIVE-SYNTHESIS, ; DIMETHYL-SULFOXIDE, ; INNER SALT, ; ALDEHYDES, ; AMIDES, ; GENERATION, ; NITRILES, ; KETONES, ; ESTERS, ; DERIVATIVES
Publication Date
2017-01
Journal
JOURNAL OF ORGANIC CHEMISTRY, v.82, no.2, pp.1046 - 1052
Publisher
AMER CHEMICAL SOC
Abstract
The Burgess reagent ([methoxycarbonylsulfamoyl]triethylammonium hydroxide) has historically found utility as a dehydrating agent. Herein we show that, 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, and can be combined with other transformations (e.g., Wittig olefinations). A mechanism similar to those described for the Pfitzner-Moffatt and Swern oxidations is proposed © 2016 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/3589
DOI
10.1021/acs.joc.6b02629
ISSN
0022-3263
Appears in Collections:
Center for Multidimensional Carbon Materials(다차원 탄소재료 연구단) > 1. Journal Papers (저널논문)
Files in This Item:
12. acs.joc.pdfDownload

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