HYDROZIRCONATION OF (E)-3-METHOXY-1-PHENYL-1-PROPENE AND (E)-3-PHENYL-2-PROPENOL

Hydrozirconation-deuterolysis of (E)-3-methoxy-1-phenyl-1-propene was found to give alpha- and omega-deuterated propylbenzenes after elimination of the ether function. An unforeseen high degree of benzylic substitution in the propylbenzenes was observed. In an effort to account for the regiochemical outcome of the reaction, hydrozirconation of propenylbenzenes with mixed reagents and deuterozirconation was investigated. Hydrozirconation of (E)-3-phenyl-2-propenol results in loss of the hydroxyl group to only a small extent, and after hydrozirconation and deuterolysis fair yields of benzenepropan-gamma-d-ol are formed. Carbonyl insertion into 3-hydroxyl-1-phenyl-1-zirconocene-propane gives low yields of the lactone dihydro-3-phenyl-2(3H)-furanone.