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 Научная публикация

Журнал

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

Вых. Данные

Год: 2006, Том: 42, Номер: 1, Страницы: 100-106 Страниц : 7 DOI: 10.1134/S1070428006010155

Авторы

Bushmelev VA ¹ , Genaev AM ¹ , Shubin VG ¹

Организации

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

Опубликована в печати:

1 янв. 2006 г.

Web of science	WOS:000235296000015
Scopus	2-s2.0-33644988487
РИНЦ	13526455
OpenAlex	W1975435971