Studies on directed lithiation: 1. Reactivity studies on alkoxide-directed lithiation reactions. 2. NMR spectroscopic characterization of the solution structure of an asymmetric lithiation reagent

A multifaceted approach to the study of the structure and reactions of organolithium aggregates is described. The lithiation of the cyclopropyl rings of a rigid bis-cyclopropylcarbinol has been shown to occur via two sequential lithiation steps. The first lithiation occurs very rapidly compared to the lithiation of other cyclopropane rings and appears to be the result of a favorable geometric orientation of the alkoxide directing group with respect to the proton being removed. The second lithiation is the only example of a bis-cyclopropyl compound undergoing dilithiation and appears to be the result of a complex-induced proximity effect.

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

• Gallagher, Donald Joseph

• Chemistry, Organic

Statement dc:rights

• Copyright 1992 Gallagher, Donald Joseph

Language dc:language

eng

Identifier

AAI9215812
(UMI)AAI9215812

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/20935