PREPARATION OF NITRILES FROM CARBOXYLIC-ACIDS - A NEW, SYNTHETICALLY USEFUL EXAMPLE OF THE SMILES REARRANGEMENT

Authors
HUBER VJ BARTSCH RA
Citation
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
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
32
Year of publication
1998
Pages
9281 - 9288
Database
ISI
SICI code
0040-4020(1998)54:32<9281:PONFC->2.0.ZU;2-K
Abstract
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.