Degenerate rearrangement of detectable 9,10-dimethyl-9-vinyl-phenanthrenium ion: 1,2-shift of the vinyl group

Degenerate rearrangement of detectable 9,10-dimethyl-9-vinyl-phenanthrenium ion: 1,2-shift of the vinyl group Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2006, Volume: 42, Number: 1, Pages: 100-106 Pages count : 7 DOI: 10.1134/S1070428006010155

Authors

Bushmelev VA ¹ , Genaev AM ¹ , Shubin VG ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Div, Norozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

Dynamic NMR study showed that 9.10-dimethyl-9-vinylphenanthrenium ion, generated under the conditions ensuring its "long life." undergoes very fast (Delta G(not equal) = 24.4 kJ/mol at -103 degrees C) degenerate 1,2-shift of the vinyl group. According to the DFT quantum-chemical calculations, the process is one-step, and the low energy of formation of the activated complex is determined by effective participation of 71 electrons of the vinyl group in delocalization of the positive charge; no such delocalization is intrinsic to the initial ion.

Bushmelev V. , Genaev A. , Shubin V.
Degenerate rearrangement of detectable 9,10-dimethyl-9-vinyl-phenanthrenium ion: 1,2-shift of the vinyl group
Russian Journal of Organic Chemistry. 2006. V.42. N1. P.100-106. DOI: 10.1134/S1070428006010155 WOS Scopus РИНЦ

Бушмелев В.А. , Генаев А.М. , Шубин В.Г.
Вырожденная перегруппировка "наблюдаемого" 9-винил-9,10-диметил-фенантренониевого иона: 1,2-сдвиг винильной группы
Журнал органической химии (RUSS J ORG CHEM+). 2006. Т.42. №1. С.107-113. РИНЦ

Published print:

Jan 1, 2006

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