Document Type
Thesis - Open Access
Award Date
1973
Degree Name
Master of Science (MS)
Department / School
Chemistry
Abstract
The stereochemistry of nucleophilic substitutions at phosphorus has been a subject of intense study. Most studies have made use of optically active reactants and products and have been hampered by the ambiguities normally associated with-such systems. In our laboratory, we introduced a new diagnostic tool which enables us to distinguish between possible stereochemical pathways. The tool, 2-substituted- 5-chloromethyl-5-methyl-2-oxo-1,3,2-dioxaphosphorinan, allows us to study substitutions at phosphorus without resorting to optically active substrates. The object of our study was to determine the mechanism of nucleophilic substitutions at thiophosphoryl centers. To accomplish this objective, a series of 2-substituted-5-chloromethyl-5-methyl-2- thio-1,3,2-dioxaphosphorinans were prepared and employed as substrates. The stereochemical consequences due to a change in the basicity of nucleophiles, stability of leaving groups, polarity of solvents and added salts was determined. A comparison of the effects upon thiophosphates and phosphates was made.
Library of Congress Subject Headings
Phosphorus
South Dakota State University Theses
Format
application/pdf
Number of Pages
94
Publisher
South Dakota State University
Recommended Citation
Tsay, Yuh-Geng, "Nucleophilic Substitution at Phosphorus : Phosphorothioates" (1973). Electronic Theses and Dissertations. 3967.
https://openprairie.sdstate.edu/etd/3967