This paper reports a novel ruthenium catalyzed regioselective copolymerization reaction between anthrone, fluorenone or xanthone and alpha,omega-dienes such as 1,3-divinyltetramethyldisiloxane and 3,3,6,6-tetramethyl-3,6-disila-1,7-octadiene. This reaction involves the ruthenium catalyzed regioselective Anti-Markovnikov insertion of the carbon-carbon double bonds of the alpha,omega-dienes into the aromatic carbon-hydrogen bonds which are ortho to the carbonyl group of anthrone, fluorenone or xanthone. Similar ruthenium catalyzed copolymerization reactions between acetophenone and alpha,omega-dienes [1] have been recently reported as have reactions between acetophenone and alkenes to yield monomeric ortho-alkyl substituted acetophenones [2].