Cyclization reactions of long-lived 10,10-dimethyl-9-phenylethynyl-9,10-dihydrophenanthren-9-yl cation

Cyclization reactions of long-lived 10,10-dimethyl-9-phenylethynyl-9,10-dihydrophenanthren-9-yl cation Full article

Journal

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

Output data

Year: 2013, Volume: 49, Number: 9, Pages: 1313-1321 Pages count : 9 DOI: 10.1134/S1070428013090121

Authors

Sal'nikov G.E. ¹ , Genaev A.M. ¹ , Bushmelev V.A. 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, long-lived 10,10-dimethyl-9-phenylethynyl-9,10-dihydrophenanthren-9-ylium in acid medium undergoes cyclization whose direction is determined by the acidity of the medium. The cyclization in HSO3F-SbF5 superacid involves the aromatic ring in the phenanthrene core as nucleophilic component and yields 5a,6-dimethyl-4-phenyl-4,5,5a,6-tetrahydroacephenantrylene-4,6-bis(ylium). In trifluoroacetic acid the nucleophilic component is the side-chain phenyl group, and the cyclization product is neutral 8b,14b-dimethyl-8b,14b-dihydrobenzo[g]chrysen-10-yl trifluoroacetate. Both cyclization directions are observed in moderate-strength trifluoromethanesulfonic acid.

Sal'nikov G.E. , Genaev A.M. , Bushmelev V.A. , Shubin V.G.
Cyclization reactions of long-lived 10,10-dimethyl-9-phenylethynyl-9,10-dihydrophenanthren-9-yl cation
Russian Journal of Organic Chemistry. 2013. V.49. N9. P.1313-1321. DOI: 10.1134/S1070428013090121 WOS Scopus РИНЦ

Сальников Г.Е. , Генаев А.М. , Бушмелев В.А. , Шубин В.Г.
Реакции циклизации долгоживущего 9,9-диметил-10-фенилэтинилфенантренониевого катиона
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №9. С.1328-1336. РИНЦ

Published print:	Sep 1, 2013
Published online:	Oct 12, 2013

Web of science	WOS:000325617200012
Scopus	2-s2.0-84886923551
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