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-phenylprop ene with deuterium content on all carbons of the propyl chain. A deute rium effect of 2.3 is observed in comparison to the rearrangement of u ndeuterated 3-phenylpropene, Competition experiments reveal an intermo lecular D transfer. The results are consistent with a stereospecific s yn 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.