Chunmei Gao, D. Cao, Sheyang Xu
Mar 24, 2006
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0
Influential Citations
20
Citations
Journal
The Journal of organic chemistry
Abstract
10-Benzyl-9,10-dihydroanthracen-9-ols, having high electron densities in the benzene ring, exhibit in the presence of acid a transannular ring closure to the corresponding homotriptycenes in almost quantitative yields. Since the starting compounds are easily accessible from 9(10H)-anthracenone, this process represents the most facile route to such pentacyclic systems. An electron-releasing methoxy group enables the intramolecular electrophilic substitution in its para position. In the absence of such an activation, a number of alternative processes can occur, namely the acid-catalyzed dehydration to anthracene derivatives with (R not = H) or without (R = H) rearrangement or a disproportionation reaction of the secondary alcohol to the corresponding ketone and hydrocarbon.