A facile method for the conversion of certain 9,10-anthraquinones to anthracenes via successive heterogeneous alcoholic sodium borohydride reductions and dehydrations has been developed. Several halo-and methyl-substituted anthracenes have been prepared by this procedure and the intermediate 9,10-dihydroxy-9,10-dihydroanthracenes and enthrones have been isolated and characterized. Ir and nmr spectroscopy have been employed for determination of the isomer distribution of 9,10-dihydroxy-9,10-dihydroanthracenes and unsymmetrically substituted enthrones.

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Abstract9,10‐Bis(hydroxymethyl)triptycene, 9,10‐dihydro‐9,10‐bis(hydroxymethyl)‐9,10‐ethanoanthracene, 9,10‐dihydro‐9,10‐bis(hydroxymethyl)‐9,10‐(2,3‐bicyclo[2.2.1] heptano)‐anthracene, 9,10‐dihydro‐9,10‐bis(hydroxymethyl)‐N‐phenyl‐9,10‐ethanoanthracene‐11,12‐dicarboximide, and 9,10‐bis(carbethoxy)triptycene have been prepared and employed as modifying agents to improve the physical properties of polyesters such as poly(ethylene terephthalate). Especially noteworthy are the high glass transition temperatures (Tg) which can be obtained.

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