Quinones Experimental Procedure

The synthetic procedure described is based on that reported earlier for the synthesis on a smaller scale of anthracene, benz[a]anthracene, chrysene, dibenz[a,c]anthracene, and phenanthrene in excellent yields from the corresponding quinones. Although reduction of quinones with HI and phosphorus was described in the older literature, relatively drastic conditions were employed and mixtures of polyhydrogenated derivatives were the principal products. The relatively milder experimental procedure employed herein appears generally applicable to the reduction of both ortho- and para-quinones directly to the fully aromatic polycyclic arenes. The method is apparently inapplicable to quinones having an olefinic bond, such as o-naphthoquinone, since an analogous reaction of the latter provides a product of undetermined structure (unpublished result). As shown previously, phenols and hydro-quinones, implicated as intermediates in the reduction of quinones by HI, can also be smoothly deoxygenated to fully aromatic polycyclic arenes under conditions similar to those described herein. 

Quinones, J., Grambow, B., Loida, A. Geckeis, H. 1996. Coprecipitation phenomena during spent fuel dissolution. Part 1 Experimental procedure and initial results on trivalent ion behavior. Journal of Nuclear Materials, 238, 38-43. 

Isoprenylated Quinones.—A review has been published on the chemistry, distribution, and functioning of vitamins A new volume in the Methods in Enzymology series contains experimental procedures used in the ubiquinone and vitamin K fields. 

Simple experimental procedures are known for generating the two different types of acid oxygen groups on carbon (Cookson, 1978). Surface oxides developed by chemical treatment and dry oxidation at temperatures <400 °C are mainly the carboxyl and hydroxyl types. At temperatures >400 °C, the dry oxidation treatment yields mainly carbonyl groups (in the form of quinone and hydroquinone). 

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