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Preparation of nitriles from carboxylic acids: A new, synthetically useful example of the Smiles rearrangement

✍ Scribed by Vincent J. Huber; Richard A. Bartsch

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 435 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00581-x

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✦ Synopsis

Reaction of 2,4-dinitrobenzenesulfonamide with acyl chlorides in the presence of excess triethylamine produces the corresponding nitrile in good to fair yields. Mechanistic studies indicate that the reaction proceeds via a Smiles rearrangement of the initially formed N-(2,4dinitrohenzenesulfonyl)amide to form the nitrile, 2,4-dinitrophenol and sulfur dioxide.

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