The Synthesis and Study of Polycyclic Aromatic Systems

MacPherson, Ian Alexander (1963) The Synthesis and Study of Polycyclic Aromatic Systems. PhD thesis, University of Glasgow.

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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.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1963
Depositing User: Enlighten Team
Unique ID: glathesis:1963-79464
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 05 Mar 2020 09:19
Last Modified: 05 Mar 2020 09:19

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