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The mechanism of the nitrosation of enolate anion of acetone [CH3COCH2]- (1) with methyl nitrite CH3ONO (2) via an "open-chain" transition state without Na+ in the C-N bond formation process was studied by the ab initio MO method. The complex [CH3COCH2NO(OCH3)]- (C-II) was first formed from the adduct (C-I) of 1 and 2 through the transition state (TSI). Finally, E-1-hydroxyimino-2-oxo-propane CH3COCH=NOH (3E), together with Z-form (3Z), was obtained by way of the elimination process. It has become apparent that 3E is formed when C-II-A is produced in the C-N bond formation process.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Ab Initio Molecular Orbital Study of Reactivity of Active Alkyl Groups. IV. Nitrosation of Acyclic Carbonyl Compound with Methyl Nitrite via "Open-Chain" Transition State.