Activation of DMSO for Swern-type oxidation by 1,1-dichlorocycloheptatriene
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NOTICE: this is the author’s version of a work that was accepted for publication in the journal Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in the journal Tetrahedron Letters, Vol.55, No.50 (2014). DOI: http://doi.org/10.1016/j.tetlet.2014.10.100
A new dimethylsulfoxide activation method employing 1,1-dichlorocycloheptatriene has been developed for a mild Swern-type oxidation of a variety of alcohols. The carbonyl products can be obtained in good to excellent yields from this operationally simple and efficient method. This work is the first report of dimethylsulfoxide activation by a simple chlorinated hydrocarbon reagent, which has the unique ability of equilibrating to its reactive aromatic cationic form.
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