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 |
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Authors: | Niiya T Ikeda H Yukawa M Goto Y |
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Institution: | Faculty of Pharmaceutical Sciences, Fukuoka University, Japan. niiya@fukuoka-u.ac.jp |
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Abstract: | 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. |
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