
TY  - JOUR
A1  - Kelly, W 
A1  - Shannon, JS 
T1  - Chemistry of Polynuclear Compounds. IV. The Reduction of Polynuclear Quinones with cyclohexyl-<I>p</I>-toluene Sulphonate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1960
VL  - 13
IS  - 1
SP  - 103
EP  - 109
KW  - 
UR  - https://doi.org/10.1071/CH9600103 
N2  - 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. 
ER  -

