I. THE SYNTHESIS AND REACTIONS OF CHIRAL 1,3,2-OXAZAPHOSPHOLANE DERIVATIVES. II. KINETIC AND MECHANISTIC STUDIES OF POLYETHER OMEGA-PHASE CATALYZED REACTIONS OF POTASSIUM-CYANIDE WITH BENZYL BROMIDE IN NON-POLAR, APROTIC SOLVENT TOLUENE

Part I of this thesis describes the synthesis and reactions of chiral substituted 1,3,2-dioxazaphospholane ring or the 1,3,2-oxazaphospholidine ring using various methods.;Part II of this thesis addresses the nature of omega-phase catalysis. Kinetic studies of the 18-crown-6 catalyzed reaction of benzylbromide with potassium acetate showed that the rate of reactivity was dramatically enhanced by the addition of trace amounts of water, but decreased past an optimum volume of added water. Acyclic polyethers such as diglyme, triglyme or tetraglyme did not participate in the omega-phase formation and the rates of these polyether catalyzed reactions of benzyl bromide with potassium cyanide in refluxing toluene did not reflect the typical rate profile of omega-phase catalysis. Finally, kinetic studies of 18-crown-6 catalyzed reactions of benzyl bromide with potassium cyanide at 85;An unseparable mixture of two diastereomers with a ratio of 70:30 was obtained at the end of the synthesis. The reactions of the diastereomer mixtures with acyl halide led to ring opened products.