A Rapid and Efficient Method for Dehydration of Primary Amides to Nitriles. Preparation of Acrylonitrile Derivatives
- 1 January 1980
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 10 (6) , 479-487
- https://doi.org/10.1080/00397918008064272
Abstract
Chloromethylene iminium salts (Vilsmeier reagents) have a long history and thoroughly investigated chemistry(1). Chloro-N, N-dimethylforminium chloride 1 is most conveniently generated by the reaction of N, N-dimethylformamide (DMF) with oxalyl chloride(2). The reagent has also been obtained using thicnyl chloride at elevated temperature and a variety of acid chlorides(1b). The literature describes several examples of the use of thionyl chloride in combination with DMF in which 1 or a related species is thought to function as the reactive intermediate in the transformation of amides to nitriles(3).Keywords
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