Quantum-chemical investigation of the mechanism of nucleophilic addition of Cl− to the triple bond of methyl acetylenedicarboxylate
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A quantum-chemical investigation of the mechanism of the nucleophilic oxidative addition of Cl− to methyl acetylenedicarboxylate was undertaken by the MNDO-PM3 method. Each stage of the two-stage mechanism involves the addition of Cl− to the carbon-carbon multiple bond of the substrate with subsequent one-electron oxidation of the intermediates.
KeywordsTriple Bond Nucleophilic Addition Chloride Anion Acetylenedicarboxylate Acetylene Molecule
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- 1.N. M. Vitkovskaya, V. B. Kobychev, N. Yu. Matveenko, et al., Izv. Akad. Nauk. Ser. Khim., No. 8, 1793–1796 (1990).Google Scholar
- 2.N. M. Vitkovskaya, O. Yu. Dolgucheva, F. S. Dubnikov, and B. A. Trofimov, Izv. Akad. Nauk. Ser. Khim., No. 6, 1339–1342 (1988).Google Scholar
- 3.N. M. Klimenko, K. V. Bozhenko, V. V. Yakobson, et al., Teor. Éksp. Khim.,28, No. 1, 5–11 (1992).Google Scholar
- 4.N. M. Klimenko, K. V. Bozhenko, V. M. Cheskin, and O. M. Temkin, Izv. Akad. Nauk. Ser. Khim., No. 12, 2373–2377 (1995).Google Scholar
- 5.N. N. Il’chenko, Yu. A. Serguchev, L. G. Gorb, et al., Zh. Org. Khim.,65, No. 10, 1705–1710 (1995).Google Scholar
- 6.E. A. Shilov and A. E. Shilov, Ukr. Khim. Zh.,20, No. 3, 279–281 (1954).Google Scholar
- 7.A. Gorgues, D. Stephan, and J. Cousseau, J. Chem. Soc. Chem. Commun., 1493–1494 (1989).Google Scholar