The Utilization of Sulfur, Sulfenyl, Selenenyl, and Seleninyl Chlorides in the Conversion of Aldoximes to Nitriles

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.