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Title: The synthesis and study of polycyclic aromatic systems
Author: MacPherson, Ian Alexander
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1963
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A comparative study is made of the properties and reactions of the two isomeric hydrocarbons, 7,15-dihydroheptazethrene and 1.14,11.12-dibenzo-5,7-dihydropentacene. A similar investigation is carried out on hydro-derivatives of 5. 6-dibenzo-zethrene and 1.2,4.5,6.7-tribenzotetracene. A chloro-derivative of 5. 6,12.13-dibenzozethrene is synthesised. The behaviour of heptazethrene (I) and 5. 6-benzozethrene (III) as normal aromatic hydrocarbons and the failure to observe any compound which could have the carbon skeleton of either 1.14,11.12-dibenzopentacene (II) or 1.2,4.5,6.7-tribenzotetracene (IV) are explained by the latter two compounds having no Kekule structure, while the single Kekule structures of heptazethrene (I) and 5.6-benzozethrene (III) are considered sufficient to ensure normal aromatic character. Dinaphtho-(2'.3' 1.2), (2".3":6.7)-pyrene (V), anthraceno-(2'.3':1.2)-pyrene (VI) and 1.14,4.5,9.10,13.14-tetrabenzoheptacene (VII) are synthesised. The absorption spectra of these hydrocarbons are discussed with relation to other benzologues of pyrene and electronic structures are proposed for hydrocarbons of this type. The reduction of 1,2,4,5-tetrabenzoylbenzene (VIII) with copper powder in sulphuric acid is investigated with a view to the possible preparation of a compound having a bond of the Dewar type. The major product is found to be 5,6-dibenzoyl-1,3-diphenylisobenzofuran (IX). The azine derivative of this diketone (X) is found to be closely related to 1,3-diphenyl-2',3'-isonaphthofuran (XI), which is obtained by reduction of 2,3-dibenzoylnaphthalene (XII). XI is the first example of a compound containing the 2,3-naphthoquinonoid system.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available