Photolytic Conversion of Cyclohexane to Cyclohexanone Oxime

Nitrosyl chloride reacts with aliphatic hydrocarbons at room temperature under the influence of light to give a complex mixture of substitution products. When the reaction is run on cyclohexane at —25°, however, the pure oxime hydrochloride crystallizes from the reaction mixture with virtually no side products. 

Caution Nitrosyl chloride is an extremely corrosive gas, and all operations with it should be carried out in a hood. 

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