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Burgess Reagent Facilitated Alcohol Oxidations in DMSO
Prakash R Sultane1, Christopher W Bielawski1,2
1Center for Multidimensional Carbon Materials (CMCM), Institute for Basic Science (IBS) , Ulsan 44919, Republic of Korea.
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.
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