Acid-Catalyzed Cyclization of Anthracenol Derivatives to Homotriptycenes

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-04, Vol.71 (8), p.3071-3076
Main Authors: Gao, Chunmei, Cao, Derong, Xu, Sheyang, Meier, Herbert
Format: Article
Language:English
Subjects:
Acids - chemistry
Anthracenes - chemistry
Catalysis
Chemistry
Condensed benzenic and aromatic compounds
Crystallography, X-Ray
Cyclization
Exact sciences and technology
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Organic chemistry
Preparations and properties
Protons
Temperature
Water - chemistry
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Summary: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 ≠ H) or without (R = H) rearrangement or a disproportionation reaction of the secondary alcohol to the corresponding ketone and hydrocarbon.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0526791