The reaction of aliphatic hydrocarbons with nitrosyl chloride under the influence of light was first described by Lynn in 1913 (1).From this work it was shown that solutions of nitrosyl chloride in n-heptane on exposure to sunlight would form ketoximes and certain "blue oils." Ammonium chloride and hydroxylamine were also claimed to have been isolated.Later Mitchell and Carson suggested that the "blue oils" were actually chloronitroso derivatives of the hydrocarbons and not the nitroso tautomer of a ketoxime as Lynn originally suggested (2).No efforts were made in this early work to determine the conditions for optimum yields of oxime or to prevent side reactions.From results in the literature and work which we have carried out, it appears that the following reaction scheme may represent the routes by which cyclohexanone oxime and the principal by-products are formed.
Failure to resolve the aryl olefins II, III, IV and V was reported in the preceding paper.1 Compound I, on the other hand, was resolved2 and an active form had a half-life period of 173 minutes in ra-butanol at 44°. The difference between I and
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