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Aspects of coronene chemistry.

Family, Haeedeh. (1974) Aspects of coronene chemistry. Doctoral thesis, University of Surrey (United Kingdom)..

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a) The chromatographic behaviour of mono-, di-, and trinitrocoronenes (of appropriate empirical formula), prepared as described in the literature suggested that, the dinitrocoronene was contaminated with some nitrocoronene; and that the trinitrocoronene contained some dinitro- and nitrocoronenes, while nitrocoronene was a single entity. b) Few halogenocoronenes have been reported in the literature. The halogenation of coronene via mercura-tion was attempted for the preparation of bromo- and iodocoronene; the final products were unchanged starting materials. c) Oxidation of coronene and nitrocoronene, gives the corresponding quinones; (1) further oxidation of coronenequinone gave a dicarboxylic acid. The similar oxidation of nitrocoronenequinone was then attempted; no pure product was obtained. The purpose of this exercise was to establish the structure of the expected nitrodicarboxylic acid by degradation studies and so arrive at the structure of the quinone. (2) Coronenequinone reacted with o-phenylenediamines to give phenazines. It also interacted with ethylenediamine to give the corresponding quinoxaline. Some phenazines and the quinoxaline were characterised, but they did not have appropriate solubilities in non-aromatic solvents which would have enabled n. m. r. studies to be carried out. (3) The reductive acetylation of coronenequinone gives 1,2-diacetoxycoronene. The preparation from it of 1,2-dihydroxycoronene was not successful. The nitration of the diester with acetylnitrate was not effected by acetylnitrate and the starting material was recovered. The use of fuming nitric acid gave a dark red product which had analytical figures close to a compound with the empirical formula of C[5]H[2]NO[3]. The reductive acetylation of nitrocoronenequinone has been studied.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
Family, Haeedeh.
Date : 1974
Contributors :
Additional Information : Thesis (M.Phil.)--University of Surrey (United Kingdom), 1974.
Depositing User : EPrints Services
Date Deposited : 22 Jun 2018 13:01
Last Modified : 06 Nov 2018 16:52

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