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 |
|
||
| Affiliations |
|
Abstract:
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.
Cite:
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 OpenAlex
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 OpenAlex
Original:
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
Реакции циклизации долгоживущего 9,9-диметил-10-фенилэтинилфенантренониевого катиона
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №9. С.1328-1336. РИНЦ
Dates:
| Published print: | Sep 1, 2013 |
| Published online: | Oct 12, 2013 |
Identifiers:
| Web of science: | WOS:000325617200012 |
| Scopus: | 2-s2.0-84886923551 |
| Elibrary: | 21886597 |
| OpenAlex: | W2044517668 |