Abstract
It was discovered by means of dynamic NMR that the 1-(cis-1-methylprop-1-en-1-yl)-1,2-dimethyl-acenaphthylenonium ion generated under conditions of “long life” for carbocations underwent fast (ΔG#35.8 kJ mol−1 at −103°C) degenerate 1,2-shift of the cis-dimethylvinyl group. Quantum-chemical calculations by DFT method predict lower rate of 1,2-shift for the trans-dimethylvinyl group compared to cis-dimethylvinyl group and dependence on the cations conformation of the rates of these processes and of the rearrangement mechanism into the ions of phenalenyl type.
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Original Russian Text © A.V. Eremkin, O.V. Ershov, S.N. Mol’kov, V.P. Sheverdov, O.E. Nasakin, Ya.S. Kayukov, V.A. Tafeenko, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, no. 2, pp. 210–214.
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Eremkin, A.V., Ershov, O.V., Mol’kov, S.N. et al. Reaction of tetracyanoethylene with aldehydes. Synthesis of 6-imino-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitriles. Russ J Org Chem 42, 193–197 (2006). https://doi.org/10.1134/S1070428002120060
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DOI: https://doi.org/10.1134/S1070428002120060