Irradiation of N-nitroso-N-methylacetamide in methanol solution yields N-methylacetamide, nitrous oxide, and formaldehyde. In isopropyl alcohol the products are N-methylacetamide, nitrous oxide, and acetone. When cyclohexene is used as solvent, the products are N-methylacetamide and cyclohexenone oxime. A reaction mechanism is proposed which involves the formation of the amide radical and hydrogen abstraction by this radical. N-Methyl-N-nitrosovaleramide, when photolyzed in either methanol or benzene, yields N-methylvaleramide. The closely related N-nitroso-N-pentylacetamide yields, in addition to the expected N-pentylacetamide, N-(4-oximinol-pentyl)acetamide. The latter compound must arise from an intramolecular hydrogen transfer. A rationalization is proposed to account for the occurrence of an intramolecular hydrogen transfer in some amide radicals and the absence of such a reaction in others.
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