Document Type

Thesis - Open Access

Award Date


Degree Name

Master of Science (MS)

Department / School


First Advisor

William S. Wadsworth, Jr.


Our studies entail the use of a model system, the 2-substituted-5-chloromethyl-5-methyl-2-oxo-1,3,2-dioxaphosphorinan whose chemistry has been outlined in a number of publications. A phosphorian ring system is found in cyclic AMP and is the central structural feature of cyclophosphamides, which are anticancer drugs. The goal of our research project is to study the effect of metal ions in methanolysis of phosphorus (V) substrates. We have attempted to answer which metal ions are effective as catalysts and their relative efficiency. In the study of these problems, we are examining catalytic specificity of the displacement of specific ligands. The stereochemistry of the reaction, and whether an inversion or retention process has taken place are major directions of our research. Our studies involve products which are normally crystalline, and we analyze the stereochemistry by proton NMR. We have synthesized numerous 2-substituted phosphorinans and subjected them to methanolysis reactions. Reagent grade methanol is used as a solvent with molar equivalents of reactant to metal cation. The product mixtures are obtained by swamping alcoholic solutions with dilute hydrochloric acid, extracting with methylene chloride and washing the extract with dilute potassium hydroxide or dilute hydrochloric acid. work-up conditions. The product ratios do not change under work-up conditions.

Library of Congress Subject Headings


Metal ions

South Dakota State University Theses



Number of Pages



South Dakota State University