Ozonolysis of polycyclic aromatics. V. Naphthacene and 5,12-NAPHTHACENEQUINONE (cas 1090-13-7)☆☆☆★

Add time:08/14/2019    Source:sciencedirect.com

Ozonization of naphthacene (I) with one molar equivalent of ozone gave 5,12-naphthacenequinone (II). Further, I and II absorb, respectively, three and two molar equivalents of ozone to yield, presumably via Criegee's zwitterion (III), an unstable, probably monomeric ozonide (IV) in inert solvent methylene chloride, and a dimethoxy peracetal (V) in methanol. IV and V have been oxidized to 2,3-anthraquinonedicarboxylic acid (VI). VI was characterized by esterification to 2,3-dicarbomethoxyanthraquinone (VII), dehydration to 2,3-anthraquinonedicarboxylic anhydride (VIII), reduction to 2,3-anthracenedicarboxylic acid (IX) and its anhydride (X), and decarboxylation to anthraquinone (XI). These ozonolysis results are rationalized in terms of the initial addition of ozone to the conjugate 5,12-positions of I to give IIvia transition state Ia, followed by the addition of ozone to the 1,2- and 3,4-bonds of IIvia transition state IIa∗ to give the observed ozonolysis products.

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