Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 2, Pages 1046-1052Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02629
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Funding
- IBS [IBS-R019-D1]
- Ministry of education
- National Research Foundation of Korea
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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.
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