Thesis - Open Access
Master of Science (MS)
William Wadsworth, Jr.
From these results the following conclusions may be drawn: 1. The stereochemistry of nucleophilic substitution at phosphorus is influenced by the basicity of the leaving group with the more basic leaving group favoring retention. 2. Lithium ion diverts the reaction to retention by forming an intimate ion-pair with the nucleophile which then attacks phosphorus. This associated ion is less reactive than the unassociated nucleophile. 3. For the retention mechanism the leaving group participates in the rate determining step. 4. The mechanism for retention entails a more sterically unfavorable configuration than for inversion.
Library of Congress Subject Headings
South Dakota State University
Bauman, Mike, "Nucleophilic Substitution at Phosphorus in Six-Membered Ring Phosphate Esters" (1978). Electronic Theses and Dissertations. 5601.