Abstract

Abstract The reactions of ketone derivatives containing carbon-nitrogen double bond such as oximes (3), N-alkyloximes (nitrones, 11), oxime O-alkyl ethers, phenylhydrazones and semicarbazones with thiocarboxylic acids were studied for the purpose of preparing thioketones. Both 3 and 11 reacted with thiocarboxylic acids to give thioketones in good yields. The reaction did not proceed in the cases of other ketone derivatives, the starting materials being recovered. The reaction of benzophenone oxime with thiobenzoic acid gave thiobenzophenone, dibenzoyl disulfide and ammonium benzoate, while that of benzophenone-N-methylnitrone with thioacetic acid gave thiobenzophenone and N-acetyl-N-methylhydroxylamine. The mechanisms of these reactions are presented.

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