Tetrahedron p. 9281 - 9288 (1998)
Update date:2022-08-30
Topics:
Huber, Vincent J.
Bartsch, Richard A.
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.
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