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Some aspects of sulphur in organic synthesis

Some aspects of sulphur in organic synthesis
Some aspects of sulphur in organic synthesis

The development of novel synthetic methods in organic chemistry is important for it allows the construction of complex molecules by new routes. Studies were made on the anion derived from 3-dimethylamino-lphenylthioprop-l-ene with the view to developing a new a,8-unsaturated acyl anion equivalent. A new route to substituted 1,3-bis(phenylthio) alk-l-enes was discovered and is described in Chapter One. Chapter Two describes new approaches to cyclopent-2-enones. 1-Phenylthio-2-(phenylthiomethyl)cyclopent-l-ene was prepared and the anion of this reacted with a number of electrophiles. Alkylated products were hydrolysed with mercuric chloride providing a cyclopentanone-2methylidene anion equivalent and, potentially, a new general route to cyclopent-2-enones.Pyrindicin, a fungal metabolite of biological interest, is the topic of Chapter Three. The attempted synthesis of this alkaloid by several routes was not successful.

University of Southampton
Mead, Keith Thomas
Mead, Keith Thomas

Mead, Keith Thomas (1982) Some aspects of sulphur in organic synthesis. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

Abstract

The development of novel synthetic methods in organic chemistry is important for it allows the construction of complex molecules by new routes. Studies were made on the anion derived from 3-dimethylamino-lphenylthioprop-l-ene with the view to developing a new a,8-unsaturated acyl anion equivalent. A new route to substituted 1,3-bis(phenylthio) alk-l-enes was discovered and is described in Chapter One. Chapter Two describes new approaches to cyclopent-2-enones. 1-Phenylthio-2-(phenylthiomethyl)cyclopent-l-ene was prepared and the anion of this reacted with a number of electrophiles. Alkylated products were hydrolysed with mercuric chloride providing a cyclopentanone-2methylidene anion equivalent and, potentially, a new general route to cyclopent-2-enones.Pyrindicin, a fungal metabolite of biological interest, is the topic of Chapter Three. The attempted synthesis of this alkaloid by several routes was not successful.

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Published date: 1982

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Local EPrints ID: 460610
URI: http://eprints.soton.ac.uk/id/eprint/460610
PURE UUID: 9baca69e-a42e-472a-89f9-774c88a966b8

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Date deposited: 04 Jul 2022 18:25
Last modified: 04 Jul 2022 18:25

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Author: Keith Thomas Mead

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