β-KETONITROSAMINES. SYNTHETIC EQUIVALENTS OF α-METHYLENE ALKYLAMINO ANIONS (-CH2NHR).
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 powdered sodium hydroxide - sodium carbonate in DMF or THF at 25 deg C.Reaction with an alkyl 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.
Saavedra, Joseph E.,Farnsworth, David W.,Farrelly, James G.
p. 1147 - 1156
(2007/10/02)
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