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Synthesis and reactions of isocyanides using a flow reactor

Newby, James (2013) Synthesis and reactions of isocyanides using a flow reactor. PhD thesis, University of Sheffield.

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Abstract

The work described in this thesis is divided into eight chapters: Chapters one and two contain an overview of the literature surrounding the project, focussing on flow chemistry and the chemistry of the isocyanide functional group. Chapter three explains project aims and objectives, and contains information relevant to the flow machine used in this project. Chapter four describes efforts towards developing a method for the synthesis of isocyanides from primary amines using the flow reactor. A procedure for synthesising N-formamides from primary amines using either a solution-phase or solid-phase catalyst was developed, with the solid-phase catalyst giving N-formamides in quantitative yields with no requirement for purification. Alongside this methodology, a procedure for synthesising several isocyanides from N-formamides using the flow reactor was also developed. Furthermore, investigations into a one-step synthesis of isocyanides from primary amines are described. In chapter five a group of medicinally-valuable heterocyclic compounds were synthesised via a 3-component Ugi reaction using the flow machine. The results of the investigation were compared to literature examples of similar reactions performed using either batch or microwave irradiation techniques. In chapter six a 4-component Ugi reaction was used to synthesise a 40-compound library of cyclic amides in order to showcase the benefit of using a flow reactor to perform multiple similar reactions in sequence. The method developed was also applied to the synthesis of a natural product methyl-glutamic acid. Chapter seven discusses possible future projects that build upon the methodology developed, and chapter eight contains data of all experimental procedures featured in this thesis.

Item Type: Thesis (PhD)
Keywords: chemistry, flow, isocyanides, multicomponent reactions
Academic Units: The University of Sheffield > Faculty of Science (Sheffield) > Chemistry (Sheffield)
Identification Number/EthosID: uk.bl.ethos.577403
Depositing User: Mr James Newby
Date Deposited: 15 Jul 2013 14:16
Last Modified: 03 Oct 2016 10:45
URI: http://etheses.whiterose.ac.uk/id/eprint/4127

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