Rearrangements of 1-(1-methylprop-1-en-1-yl)-1,2-dimethylacenaphtyylenonium ions

Autor:	Vyacheslav G. Shubin, V. A. Bushmelev, Alexander M. Genaev
Rok vydání:	2006
Předmět:	Chemistry Group (periodic table) Computational chemistry Organic Chemistry Carbocation Medicinal chemistry Ion
Zdroj:	Russian Journal of Organic Chemistry. 42:220-226
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428002120102
Popis:	It was discovered by means of dynamic NMR that the 1-(cis-1-methylprop-1-en-1-yl)-1,2-dimethylacenaphthylenonium 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.
Databáze:	OpenAIRE
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