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Abstract
Abstract The comparative usefulness of six sulfur, sulfenyl, selenenyl, and seleninyl chlorides towards aldoximes in the presence of a base were examined under similar reaction condi-tions. The reactions of aromatic aldoximes with either sulfur dichloride (1), sulfur mono-chloride (2), or trichloromethane sulfenyl chloride (3) in either ether or chloroform at 23-35 °C after one hour resulted in 60-84% yields of nitriles. Under the same conditions, the reactions of aliphatic aldoximes with either 1, 2, or 3 gave mixtures of products, while at -40 to -30 °C, 15-22% yields of aliphatic nitriles were obtained. The reactions of aliphatic and aromatic oximes with either benzenesulfenyl chloride (4), benzene-selenenyl chloride (5), or benzeneseleninyl chloride (6) produced after fifteen minutes to three hours the corresponding nitriles in 71-96% yields at 23-35 °C.
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