Some aspects of quinonoid chemistry

Mitchell, Peter Robert King

Some aspects of quinonoid chemistry

Doctoral Thesis

1979

Publisher

University of Cape Town

Department

Department of Chemistry

Faculty

Faculty of Science

Abstract

The first part of this thesis deals with the attempts made to synthesise 4 - hydroxypiloquinone. The proposed synthesis involved the making of two correctly substituted aromatic moieties that could be joined together to give a stilbene, which on irradiation would give a phenanthrene, that could be further elaborated to give a suitable precursor to 4 - hydroxypiloquinone. All attempts to convert the precursor to the required quinone were unsuccessful. In the second part of this thesis, a number of 2 - acetyl - 3 -alkylamino - 6 - anilino - 1,4 - benzoquinones were prepared by the reaction of 2 - acetyl - 3,6 - dianilino - 1,4 - benzoquinone with alkylamines in chloroform. Irradiation of these alkylamino - p -benzoquinones with ultra-violet light gave benzoxazoles where an á -hydrogen atom was present in the alkylamino substituent, except for the cyclohexylamino - and s - butylamino - benzoquinones which gave an unstable photo-product. With t - butylamino - benzoquinone no photoreaction was observed.

Description

Includes bibliographical references.

Keywords

Organic Chemistry

Reference:

Collections

PhD / Doctoral

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