Photonitrosation of Cycloalkanes with Nitrosyl Chloride. I. Synthesis of Cyclohexanone Oxime

Abstract

The photonitrosation of cyclohexane with nitrosyl chloride was investigated. It was established that cyclohexanone oxime may be easily produced in good yield (72%) under suitable conditions. The dilution of nitrosyl chloride with hydrogen chloride was most effective for preventing the side reactions, and the photonitrosation of cyclohexane was carried out successsfully at a temperature of 10°C.The color of the reaction liquid played the role of indicator for a successful photonitrosation; the side reactions seemed not to occur practically so long as the color of the reaction liquid is yellow, and hence, the addition rate of nitrosyl chloride into cyclohexane should be controlled following the color change of reaction liquid.