A Practical One-Pot Synthesis of Soluble Hexa-p eri-hexabenzocoronene and Isolation of Its Cation-Radical Salt

A simple and practical synthesis of soluble hexa-peri-hexabenzocoronene (HBC) from readily available hexaphenylbenzene (HPB) is described. In this simple procedure, the substitution of the free para positions of the propeller-shaped HPB with tert-butyl groups and the oxidative cyclodehydrogenation t...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 68; no. 10; pp. 4071 - 4074
Main Authors Rathore, Rajendra, Burns, Carrie L
Format Journal Article
LanguageEnglish
Published American Chemical Society 16.05.2003
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Summary:A simple and practical synthesis of soluble hexa-peri-hexabenzocoronene (HBC) from readily available hexaphenylbenzene (HPB) is described. In this simple procedure, the substitution of the free para positions of the propeller-shaped HPB with tert-butyl groups and the oxidative cyclodehydrogenation to planar HBC is achieved in a one-pot reaction using ferric chloride both as a Lewis acid catalyst and as an oxidant in excellent yields. The ready availability of HBC allows the isolation of its pure cation-radical salt using a variety of chemical oxidants such as antimony pentachloride and triethyloxonium and nitrosonium hexachloroantimonate salts.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034271e