Thesis-2003-Boxhall.pdf (4.04 MB)
Synthetic routes towards chiral calix[4]resorcinarenes
thesis
posted on 2018-07-16, 09:28 authored by Jonathan Y. BoxhallThis thesis is divided into three chapters.
Chapter 1 contains a brief overview of the literature reports in the area of
calix[4]resorcinarene chemistry. The many methods available for the preparation and use
of these macrocycles, their functionalisation on both the upper and lower rims and the use
of Mannich reaction protocols for the introduction of chirality into these symmetrical
molecules are discussed.
Chapter 2 describes new methodology for the formation of a range of chiral
calix[4]resorcinarenes, most notably the formation of tetra alkyloxy
calix[4]resorcinarenes as racemic mixtures, which can then be separated as
diastereoisomers following the use of new Mannich reaction methodology for the
formation of tetra benzoxazine derivatives.
One of these enantiomerically pure resorcinarenes has been used as a catalyst in the
addition of diethylzinc to benzaldehyde.
The attempts made at deepening the cavity of these macrocycles, by utilising Sonogashira
coupling reactions, are also discussed.
Chapter 3 contains the experimental details and analytical data for the successful
reactions discussed in Chapter 2.
History
School
- Science
Department
- Chemistry
Publisher
© Jonathan Yates BoxhallPublisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Publication date
2003Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.Language
- en