Some aspects of quinonoid chemistry

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.