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Synlett 1990; 1990(12): 733-734
DOI: 10.1055/s-1990-21229
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Base-Catalyzed Autoxidation of α-Aminonitriles. An Efficient Method for Conversion of Aldehydes to Amides and 2-Amino-2-sulfenylacetonitrile to Carbamates

Tsung-Hsun Chuang* , Chau-Chen Yang, Chih-Jung Chang, Jim-Min Fang
  • *Department of Chemistry, National Taiwan University, Taipei, 10764, Taiwan, Republic of China
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Publication Date:
08 March 2002 (online)

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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.