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2. Base-Catalyzed Autoxidation of α-Aminonitriles. An Efficient Method for Conversion of Aldehydes to Amides and 2-Amino-2-sulfenylacetonitrile to Carbamates

Author

Tsung-Hsun Chuang, Jim-Min Fang, Chih-Jung Chang, and Chau-Chen Yang

Subjects
chemistry.chemical_classification, Autoxidation, Base (chemistry), Potassium, Organic Chemistry, chemistry.chemical_element, Medicinal chemistry, Catalysis, chemistry.chemical_compound, chemistry, Yield (chemistry), Alkoxide, Acetonitrile, Alkyl
Abstract

The α-aminonitriles 2, prepared from aromatic, aliphatic, and α,β-unsaturated aldehydes, undergo autoxidation in the presence of potassium tert-butoxide to give the corresponding amides 3 in high yield. The α-sulfenyl-α-aminonitrile 4 (methylphenylamino(phenylthio)acetonitrile) is converted to the alkyl N-methyl-N-phenylcarbamates 6 by concurrent autoxidation and substitution with alkoxide ions.

Published
1990
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