Doctoral Dissertations

Date of Award

12-1970

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

Donald C. Kleinfelter

Committee Members

Alexander Van Hood, John B. Vercellotti

Abstract

Part A: In this thesis research on the action of Grignard reagents with with norbornene oxide has been initiated and found to be of possible synthetic utility.

Part B: The structure of the product of the acid catalyzed dehydration of 2-p-anisylnorbornane-2, 3-cis-exo-diol in hydrochloric acid-tetrahy-drofuran has been reassigned. It was discovered, on the basis of further data, that the structure of the high melting solid was that of the dimer of the epoxide, a p-dioxane, rather than the epoxide itself. This change was proposed for many reasons. A near total nmr analysis of the compound was completed, including double irradiation experiments, an iterative computer program comparison between the theoretically generated and experimental spectra, and high temperature nmr studies. The o,o,o',o-tetra-deuterio derivative was synthesized and by means of elevated temperature nmr the free energy barrier to rotation about the aryl-norbornane bond was computed to be 19.6 kcal mole-1.

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