Hydrogen transfer from naphthenes to aromatics, coal, resid, and coal plus resid has been investigated at 430-degrees-C in a N2 atmosphere. The reaction of perhydropyrene (PHP) with anthracene (ANT) resulted in the formation of pyrene (PYR) and dihydroanthracene. The weight percents of the products formed varied according to the ratio of ANT:PHP used with a minimum appearing at a 2:1 weight ratio. Longer reaction times and high ANT:PHP ratios also yielded tetrahydroanthracene. Reactions of Illinois No. 6 coal from the Argonne Premium Coal Sample Bank with PHP, ANT, and PYR resulted in higher coal conversion with PHP and lower with ANT and PYR. Reactions of PHP with resid resulted in less retrogressive reactions occurring in the resid than with either PYR or ANT. Apparent hydrogen transfer from coal or resid to ANT was observed. Combining PHP with ANT or PYR with coal, resid, or coal plus resid yielded higher conversions and less retrogressive reactions than with ANT or PYR alone. Hydrogen transfer occurred from PHP to ANT or PYR and to the coal and resid as evinced by the increased conversion and the reaction products obtained from the model system.