Syntheses of Polycyclic Aromatic Hydrocarbons

Willicks, Winfried (1958) Syntheses of Polycyclic Aromatic Hydrocarbons. PhD thesis, University of Glasgow.

Abstract

The main body of work described in this Thesis was the synthesis of peri-aryltetracene derivatives, and the cyclisation of these to new condensed hydrocarbons, all of which contained the tetracene ring-system. Closely related to this work, however, were the syntheses of 1:2-8:9-dibenzanthrene, rubicene, and iso-rubicene. The Thesis, then, falls mainly into three interrelated parts. The first deals with the synthesis of 5-naphthyltetracene, and the condensation of this compound to 1:2-5:6-dibenzperylene, and to 1:2-5:6-7:8-tribenzfluoranthene. It was as an integral part of this study that 1:2-8:9-dibenzanthrene was synthesized, and two hydrogenated derivatives of this hydrocarbon were found to constitute the first known example of linear-angular isomerism in tetraphene-3:4-benzphenanthrene systems. The second part describes the synthesis of 5:12-dinaphthyl-tetracene, and the condensation of this coumpound to 7:8-15:16-dibenzterrylene. The remainder of the Thesis began with the synthesis of 5:12-diphenyltetracene and the cyclisation of this to 2:3-benzorubicene, and this in turn led to a full study of the synthesis of rubicene and iso-rubicene (including a new synthesis of rubicene) and several new derivatives of 2:3-benzfluoranthene. Throughout all these investigations, the absorption spectra of the numerous new compounds were examined, and this, coupled with the formation of maleic anhydride adducts, was used as an important tool in establishing the structures of the new hydrocarbons. In addition, the Annelation Principle of E. Clar was extended in the series of perylenes and terrylenes.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1958
• Depositing User: Enlighten Team
• Unique ID: glathesis:1958-79298
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 05 Mar 2020 11:01
• Last Modified: 05 Mar 2020 11:01
• URI: https://theses.gla.ac.uk/id/eprint/79298