Degenerate rearrangement of 9-isopropenyl-9,10-dimethylphenanthren-9-yl and 9,10-dimethyl-9-(trans-1-methylprop-1-en-1-yl)phenanthren-9-yl cations

Degenerate rearrangement of 9-isopropenyl-9,10-dimethylphenanthren-9-yl and 9,10-dimethyl-9-(trans-1-methylprop-1-en-1-yl)phenanthren-9-yl cations Full article

Journal

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

Output data

Year: 2006, Volume: 42, Number: 9, Pages: 1257-1263 Pages count : 7 DOI: 10.1134/S1070428006090016

Authors

Artamoshkin V.G. ^1,2 , Bushmelev V.A. ¹ , Genaev A.M. ¹ , Shubin V.G. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Div, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Pedagog Univ, Novosibirsk, Russia

H-1 NMR study has shown that long-lived 9-R-9,10-dimethylphenanthren-9-yl cations (R = isopropenyl, trans-1-methylprop-1-en-1-yl) generated in the system HSO3F-SO2ClF-CD2Cl2 at -130 degrees C undergo degenerate rearrangement via 1,2-vinyl shifts (Delta G(not equal) = 37 and 39 kJ/mol, respectively, at -88 degrees C). Analysis of the geometric parameters of the initial structures and transition states calculated by the DFT method indicates that unfavorable steric factors are responsible for the sharp deceleration of 1,2-shifts of the isopropenyl and trans-1-methylprop-1-en-1-yl groups as compared to vinyl and cis-1-methylprop-1-en-1-yl groups, respectively.

Artamoshkin V.G. , Bushmelev V.A. , Genaev A.M. , Shubin V.G.
Degenerate rearrangement of 9-isopropenyl-9,10-dimethylphenanthren-9-yl and 9,10-dimethyl-9-(trans-1-methylprop-1-en-1-yl)phenanthren-9-yl cations
Russian Journal of Organic Chemistry. 2006. V.42. N9. P.1257-1263. DOI: 10.1134/S1070428006090016 WOS Scopus РИНЦ

Артамошкин В.Г. , Бушмелев В.А. , Генаев А.М. , Шубин В.Г.
Вырожденная перегруппировка 9,10-диметил-9-(1-винил-1-метил)фенантренониевого и 9,10-диметил-9-(транс-1-метилпроп-1-ен-1-ил)фенантренониевого ионов
Журнал органической химии (RUSS J ORG CHEM+). 2006. Т.42. №9. С.1279-1285. РИНЦ

Published print:

Sep 1, 2006

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