Tetrahedron

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

VJ Huber, RA Bartsch

文献索引：Huber, Vincent J.; Bartsch, Richard A. Tetrahedron, 1998 , vol. 54, # 32 p. 9281 - 9288

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被引用次数: 33

摘要

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.