Stereoselective alkylations and rearrangements of chiral phosphonic and phosphinic acid derivatives

The stereochemical course of carbon migration from phosphorus to nitrogen and oxygen were investigated. Optically active ($\geq$99.9% e.e.) phosphonic and phosphinic azides were prepared and photolyzed in methanol to effect the phosphorus analogues of the carbonyl-Curtius rearrangement. These studies showed that carbon migration in the phosphinoyl-Curtius rearrangement proceeds with 99% net retention of configuration while the migration in the first example of the phosphonoyl-Curtius rearrangement occurs with 99.4% net retention of configuration.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Dorow, Roberta L.

Contributors dc:contributor

• Denmark, Scott E.

• Chemistry, Organic

Statement dc:rights

• Copyright 1990 Dorow, Roberta L.

Language dc:language

eng

Identifier

AAI9026171
(UMI)AAI9026171

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/20514