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

Article abstract of DOI:10.1016/S0040-4020(98)00581-X

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-(2,4- dinitrobenzenesulfonyl)amide to form the nitrile, 2,4-dinitrophenol and sulfur dioxide.