
%0 Journal Article
%A Kelly, W 
%A Shannon, JS 
%T Chemistry of Polynuclear Compounds. IV. The Reduction of Polynuclear Quinones with cyclohexyl-<I>p</I>-toluene Sulphonate
%J Australian Journal of Chemistry
%D 1960/03/01
%V 13
%N 1
%P 103-109
%K 
%R https://doi.org/10.1071/CH9600103
%U https://www.publish.csiro.au/paper/CH9600103 
%X In an investigation into the coking mechanism of coal, polynuclear quinones have been adopted as models. Using cyclohexyl-p-toluene sulphonate the following quinones have been reduced to their parent hydrocarbons : dibenzanthrone, isodibenzanthrone, pyranthrone, 4,10-dibromoanthanthrone, anthraquinone (and anthrone), 1,5-dimethoxyanthraquinone, and 1,8-dimethoxyanthraquinone. The reaction gave favourable yields compared with alternative methods, but had the advantage that substituent groups such as halogen and alkoxyl were unattacked. A mechanism is proposed involving complexing of cyclohexyl cations with the quinones, followed by hydrogen-transfer via a resonance-stabilized cyclic transition state. 
