Journal of the American Chemical Society, Vol.116, No.25, 11375-11378, 1994
Mechanistic Studies on the Rearrangement Activity of a Ring-Opening Metathesis Polymerization Catalyst - Reaction of (Ru(H2O)(6))(2+) with Unfunctionalized Olefins
The rearrangement of 3-phenylpropene-3,3-d(2) catalyzed by [RU(H2O)(6)](2+) in different solvents yields stereospecifically trans-phenylpropene with deuterium content on all carbons of the propyl chain. A deuterium effect of 2.3 is observed in comparison to the rearrangement of undeuterated 3-phenylpropene, Competition experiments reveal an intermolecular D transfer. The results are consistent with a stereospecific syn 1,2-addition-elimination of an intermediately formed metal hydride with predominant attack of the metal on position 2 of 3-phenylpropene-3,3-d(2), and also explain the selective production of trans products.