Intramolecular Reactions of Trivalent Phosphorus and Carbonyl Functions

Phosphonous diesters derived from the reaction of phenylphosphonous dichloride with 2-ketophenols readily undergo head-to-tail oxidative cyclization to yield stable tricyclic phosphoranes in cases where the carbonyl function is an aldehyde, trifluoroacetophenone, or diaryl ketone. A methyl imine function may also participate in such a reaction. Oxidative cyclization does not occur where the carbonyl group in the phosphonous diester is an ester or a sterically hindered diaryl ketone. An equilibrium between the trivalent and pentavalent forms of the product derived from 2-hydroxy-2',4,4'-trimethoxybenzophenone is reported.

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

2014

Author dc:creator

• Harper, Stephen Daniel

• Chemistry, Organic

Language dc:language

eng

Identifier

(UMI)AAI8203481

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/67291