Reactions of quinones with aromatic ethers.

Buchan, Robert

Abstract

The reactions between quinones and aromatic compounds in the presence of acids are surveyed; and a summary of the methods used for preparing triphenylenes is outlined. Mono- and di-arylquinones have been prepared by the arylation of benzoquinones with diazotised 3,4-dimethoxyaniline (Meerwein reaction). The structures of the arylquinones are determined spectroscopically and by conversion to known compounds. The aluminium chloride-catalysed reaction between benzoquinones and either veratrole or 3',4'-dimethoxyphenyl-benzoquinones gives derivatives of triphenylene-1,4:5,8-diquinone. 2-(3',4'-dimethoxyphenyl)-3-arylbenzoquinones have been cyclised in the presence of Lewis or protic acids to triphenylene-1,4-quinones. The reaction between concentrated hydrochloric acid and either 2,3-di(3',4'-dimethoxyphenyl)-benzoquinone or 5,6-dichloro-2,3-di(3',4'-dimethoxyphenyl)-benzoquinone gives 5-chloro-substituted triphenylene-1,4-quinones. A new synthesis of 2-hydroxytriphenylenes is developed by treating veratrole with chlorobenzoquinones in aqueous sulphuric acid. An attempted reaction between veratrole and 1,4-naphthaquinone in the presence of aluminium chloride gave only products derived from 1,4-naphthaquinone, one of these is a new dinaphofuran derivative, viz. 8-hydroxydinaphtho-[1,2-b:2',1'-d]furan-5,6-quinone. The structures of all compounds have been determined by both physical and chemical techniques, and mechanisms have been suggested and dicussed for new reactions.

Citation

BUCHAN, R. 1972. Reactions of quinones with aromatic ethers. Robert Gordon's Institute of Technology, PhD thesis. Hosted on OpenAIR [online]. Available from: https://doi.org/10.48526/rgu-wt-1993220

• Thesis Type: Thesis
• Deposit Date: Nov 12, 2024
• Publicly Available Date: Nov 12, 2024
• DOI: https://doi.org/10.48526/rgu-wt-1993220
• Public URL: https://rgu-repository.worktribe.com/output/1993220
• Award Date: Mar 31, 1972