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Title: Using modern synthetic techniques to conduct difficult transformations relating to the agrochemical industry
Author: Mallia, Carl James
ISNI:       0000 0004 5923 1444
Awarding Body: Durham University
Current Institution: Durham University
Date of Award: 2016
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The work described in this dissertation is divided into three chapters each discussing independent projects where either gas-liquid flow technology or microwave reactor technology was applied to organic synthesis. The first chapter describes the flow hydroxy-carbonylation of ortho-substituted iodo arenes. It was found that through the use of a “tube-in-tube” reactor to introduce the carbon monoxide gas to the reaction mixture, a number of ortho-substituted carboxylic acids could be prepared. The second part of this chapter deals with the synthesis of a herbicidal intermediate which was prepared through the carboxylation reaction with carbon dioxide (dry ice). A parallel flow process for the preparation of this herbicidal intermediate was also developed. This work was reported in one publication. In the second chapter another gas; oxygen, was used in continuous flow as an oxidant in the Chan-Lam reaction. The first part of this chapter demonstrates how a continuous process for the synthesis of a herbicidal intermediate was developed through an optimised catalytic Chan-Lam reaction which was also shown to consistently work at different scales. In the second part a more generalised catalytic Chan-Lam reaction was optimised and this lead to a small collection of C-N coupled products. This work was published in one publication. The use of 1,4-dithain-2,5-diol as a precursor for 2-mercaptoacetaldehyde was used as a building block for the synthesis of thiazoles in the third chapter. Using microwave reactor technology the optimised reaction conditions for this novel transformation was quickly achieved. A bifurcation pathway was discovered where either 2-aminothiophens or 2-substiuted thiazoles were prepared, which was demonstrated through the synthesis of a small library of compounds. This work was disclosed in two separate publications.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available