Carbocationic rearrangements of 6b,7,8,8a-tetramethyl-6b,8a-dihydrocyclobut[a]acenaphthylene: Effect of medium acidity

Rearrangements of 6b,7,8,8a-tetramethyl-6b,8a-dihydrocyclobut[a]acenaphthylene in acids were investigated by NMR spectroscopy. The initially formed 3b,4-exo,4a,5-tetramethyl-3b,4,4a,5-tetrahydro-4H-cyclopropa[a]phenalen-5-yl cation and its endo-epimer rearranged into carbocations of phenalenyl type....

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Bibliographic Details
Published in:Russian journal of organic chemistry 2009-08, Vol.45 (8), p.1175-1180
Main Authors: Bushmelev, V. A, Genaev, A. M, Sal'nikov, G. E, Shubin, V. G
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Rearrangements of 6b,7,8,8a-tetramethyl-6b,8a-dihydrocyclobut[a]acenaphthylene in acids were investigated by NMR spectroscopy. The initially formed 3b,4-exo,4a,5-tetramethyl-3b,4,4a,5-tetrahydro-4H-cyclopropa[a]phenalen-5-yl cation and its endo-epimer rearranged into carbocations of phenalenyl type. Therewith the direction and the rate of rearrangement sharply changed at relatively small variations in the medium acidity.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428009080107