Behavior of 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium: Opening of the cyclopropane ring

Behavior of 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium: Opening of the cyclopropane ring Full article

Journal

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

Output data

Year: 2011, Volume: 47, Number: 6, Pages: 862-868 Pages count : DOI: 10.1134/S1070428011060054

Authors

Genaev A. M. ¹ , Sal'nikov G. E. ¹ , Shubin V. G. ¹

Affiliations

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

According to the NMR data, opening of the cyclopropane ring in carbocations derived from 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium follows two pathways, depending on the acidity. The first pathway is protonation of the cyclopropyl group; it occurs in strongly acidic medium (HSO3F-SbF5-SO2ClF-CD2Cl2). The second pathway involves cyclopropyl-carbinyl rearrangement; it is typical of less acidic medium.

Genaev A.M. , Sal'nikov G.E. , Shubin V.G.
Behavior of 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium: Opening of the cyclopropane ring
Russian Journal of Organic Chemistry. 2011. V.47. N6. P.862-868. DOI: 10.1134/S1070428011060054 WOS Scopus РИНЦ

Генаев А.М. , Сальников Г.Е. , Шубин В.Г.
Поведение 10,10-диметил-9-циклопропил-9,10-дигидрофенантрен-9-ола в кислых средах: раскрытие циклопропанового кольца
Журнал органической химии (RUSS J ORG CHEM+). 2011. Т.47. №6. С.9-10. РИНЦ

Published print:	Jun 1, 2011
Published online:	Jul 8, 2011

Web of science	WOS:000292562900005
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