Rearrangements of long-lived carbocations derived from 9-hydroxy-1,8,9,10,10,11,12-heptamethyltricyclo[6.2.2.02,7]-dodeca-2(7),3,5,11-tetraene in superacids

Rearrangements of long-lived carbocations derived from 9-hydroxy-1,8,9,10,10,11,12-heptamethyltricyclo[6.2.2.02,7]-dodeca-2(7),3,5,11-tetraene in superacids Full article

Journal

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

Output data

Year: 2000, Volume: 36, Number: 9, Pages: 1268-1278 Pages count : 11

Authors

Genaev A.M. , Mamatyuk V.I. , Sal'nikov G.E. , Shakirov M.M. , Shubin V.G.

Affiliations

1	(Scopus) Vorozhtsov Novosibirsk Inst. of O., Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent'eva 9, Novosibirsk, 630090, Russian Federation

Rearrangements of long-lived carbocations formed from endo-9-hydroxy-1,8,9,10,10,11,12-hepta-methyltricyclo[6.2.2.02,7]dodeca-2(7),3,5,11-tetraene in the system HSO3F-SO2ClF-CD2Cl2 at -95°C and having 6,7-benzobicyclo[3.2.1]octadiene and 5,6-benzotricyclo[3.2.1.02,7]octene structures were studied by 1H and 13C NMR spectroscopy. Degenerate rearrangements of similar cations derived under the same conditions from the 9-CD3-analog of the title compound were examined by the 2H NMR method. Raising the temperature results in formation of benzobicyclo[3.3.0]octadiene (benzopentalene) structures. The calculated (MINDO/3) heats of formation of isomeric carbocations are consistent with the experimental data. The mechanisms of the observed rearrangements are discussed.

Genaev A.M. , Mamatyuk V.I. , Sal'nikov G.E. , Shakirov M.M. , Shubin V.G.
Rearrangements of long-lived carbocations derived from 9-hydroxy-1,8,9,10,10,11,12-heptamethyltricyclo[6.2.2.02,7]-dodeca-2(7),3,5,11-tetraene in superacids
Russian Journal of Organic Chemistry. 2000. V.36. N9. P.1268-1278. WOS Scopus РИНЦ

Web of science:	WOS:000168014200005
Scopus:	2-s2.0-0034257760
Elibrary:	13345409

DB	Citing
Scopus	4
Web of science	5
Elibrary	4