A Mild and Efficient Alternative to the Classical Swern Oxidation

Lidia De Luca, Giampaolo Giacomelli* and Andrea Porcheddu

*Dipartimento di Chimica, Università degli Studi di Sassari, Via Vienna 2, I-07100 Sassari, Italy

L. De Luca, G. Giacomelli, A. Porcheddu, J. Org. Chem., 2001, 66, 7907-7909.

DOI: 10.1021/jo015935s

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Abstract

A mild and efficient alternative procedure for a quantitative conversion of alcohols into the corresponding carbonyl compounds uses dimethyl sulfoxide (DMSO), activated by 2,4,6-trichloro[1,3,5]-triazine (cyanuric chloride, TCT) instead of the toxic and moisture sensitive oxalyl chloride under Swern conditions.

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proposed reaction pathway

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Key Words

Swern Oxidation, aldehydes, ketones, DMSO

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ID: J42-Y2001