Vj. Huber et Ra. Bartsch, PREPARATION OF NITRILES FROM CARBOXYLIC-ACIDS - A NEW, SYNTHETICALLY USEFUL EXAMPLE OF THE SMILES REARRANGEMENT, Tetrahedron, 54(32), 1998, pp. 9281-9288
Reaction of 2.4-dinitrobenzenesulfonamide with acyl chlorides in the p
resence of excess triethylamine produces the corresponding nitrile in
good to fair yields. Mechanistic studies indicate that the reaction pr
oceeds via a Smiles rearrangement of the initially formed N-(2,4-dinit
robenzenesulfonyl)amide to form the nitrile, 2,4-dinitrophenol and sul
fur dioxide. (C) 1998 Elsevier Science Ltd. All rights reserved.