Structure of long-lived alkynyl-substituted carbocations of the phenanthrene series and their precursors

Structure of long-lived alkynyl-substituted carbocations of the phenanthrene series and their precursors Full article

Journal

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

Output data

Year: 2013, Volume: 49, Number: 6, Pages: 853-859 Pages count : 7 DOI: 10.1134/S1070428013060092

Authors

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

Affiliations

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

According to the NMR data, 9-(R-ethynyl)-9-hydroxy-10,10-dimethyl-9,10-dihydrophenanthrenes (R = H, Me, Ph) in superacid medium (HSO3F-SO2ClF) at low temperature undergo dehydroxylation with formation of the corresponding long-lived 10,10-dimethyl-9-(R-ethynyl)-9,10-dihydrophenanthren-9-yl cations which do not isomerize to 10-(R-ethynyl)-9,10-dimethyl-9,10-dihydrophenanthren-9-ylium. In contrast, longlived 10,10-dimethyl-9-(3,3,3-trifluoroprop-1-yn-1-yl)-9,10-dihydrophenanthren-9-yl cation derived from 9-(3,3,3-trifluoroprop-1-yn-1-yl)-10,10-dimethyl-9,10-dihydrophenanthren-9-ol undergoes partial isomerization to 10-(3,3,3-trifluoroprop-1-yn-1-yl)-9,10-dimethyl-9,10-dihydrophenanthren-9-yl cation.

Bushmelev V.A. , Genaev A.M. , Sal'nikov G.E. , Shubin V.G.
Structure of long-lived alkynyl-substituted carbocations of the phenanthrene series and their precursors
Russian Journal of Organic Chemistry. 2013. V.49. N6. P.853-859. DOI: 10.1134/S1070428013060092 WOS Scopus РИНЦ

Бушмелев В.А. , Генаев А.М. , Сальников Г.Е. , Шубин В.Г.
Строение долгоживущих карбокатионов фенантренового ряда с алкинильными группами и их предшественников
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №6. С.870-875. РИНЦ

Published print:	Jun 1, 2013
Published online:	Jul 6, 2013

Web of science	WOS:000321522400009
Scopus	2-s2.0-84880005953
Elibrary	20442391
OpenAlex	W2011351178