Abstract
Abstract β-Ketonitrosamines are important in the study of nitrosamine metabolism, carcinogenesis and in vivo alkylation. The enhanced acidity of protons at the α-carbon, as well as the ease of fragmentation of the title compounds establishes them as synthetic equivalents of α-methylene alkylamino anions (−CH2NHR). Anion formation is carried out with powered sodium hydroxide-sodium carbonate in DMF or THF at 25°C. Reaction with an alky halide gives a good yield of the alkylated product. Retro-Claisen cleavage in aqueous basic media gives the corresponding dialkyl-nitrosamine or, with D2O, the deuterated analog.
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