De Novo Synthesis of Phenols
Author(s)
Johns, Stephen Christopher
Type
Thesis
Abstract
This thesis is divided into three chapters. In the first, the methods currently available for the synthesis of
phenols from acyclic precursors are reviewed. The review concentrates on methods that have been used
to form a range of phenols and is divided up according to the type of chemistry employed. The second
chapter describes the development of a novel route to phenols. Initial optimisation results are described
first, followed by the synthesis of a library of phenols. The majority of these have not been reported
previously. The attempted extension of this work to the formation of anilines, nitrobenzenes and more
highly oxygenated aromatics is also presented. Finally, work towards the synthesis of the aglycone of
pseudopterosin A is described, following a route that would utilise the phenol-forming chemistry in a
more complex natural product environment. The final section details the experimental procedures used
to form the compounds described in section two, along with associated spectroscopic data.
phenols from acyclic precursors are reviewed. The review concentrates on methods that have been used
to form a range of phenols and is divided up according to the type of chemistry employed. The second
chapter describes the development of a novel route to phenols. Initial optimisation results are described
first, followed by the synthesis of a library of phenols. The majority of these have not been reported
previously. The attempted extension of this work to the formation of anilines, nitrobenzenes and more
highly oxygenated aromatics is also presented. Finally, work towards the synthesis of the aglycone of
pseudopterosin A is described, following a route that would utilise the phenol-forming chemistry in a
more complex natural product environment. The final section details the experimental procedures used
to form the compounds described in section two, along with associated spectroscopic data.
Date Issued
2008-09
Date Awarded
2009-02
Copyright Statement
Attribution NoDerivatives 4.0 International Licence (CC BY-ND)
Advisor
Craig, Donald
Creator
Johns, Stephen Christopher
Publisher Department
Chemistry
Publisher Institution
Imperial College London
Qualification Level
Doctoral
Qualification Name
Doctor of Philosophy (PhD)