Reactions of quinones with aromatic ethers.

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.

Name dc:type.qualificationname

PhD

Level dc:type.qualificationlevel

Doctoral

Grantor dc:publisher.institution

Robert Gordon's Institute of Technology

Year dc:date.issued

1972

Author dc:creator

• Buchan, Robert

Advisor dc:contributor.advisor

• O.C. Musgrave

• Quinones
• Aromatic compounds
• Triphenylenes
• Meerwein reaction
• Arylation
• Spectroscopy
• Synthesis

Language dc:language

en

Identifier

oai:rgu-repository.worktribe.com:1993220
https://doi.org/10.48526/rgu-wt-1993220

OAI identifier oai:identifier

oai:rgu-repository.worktribe.com:1993220