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The novel rearrangement of 1-acetyl-1-methylcyclohexa-2,5-diene

Pavey, Andrew 2015. The novel rearrangement of 1-acetyl-1-methylcyclohexa-2,5-diene. MPhil Thesis, Cardiff University.
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Abstract

This thesis describes the results of the research into the novel rearrangement of 1-acetyl-1-methylcyclohexa-2,5-diene under basic conditions. The rearrangement involves the migration of an acetyl group around the cyclohexadiene ring. The rearrangement occurs via a cyclopropane intermediate, to produce a mixture of two isomers. The study involves calculations that evaluate the feasibility of the proposed mechanism. This is coupled with the experimental data for the rearrangement with a range of alkylating agents. Chapter 1 presents a description of previous work carried out by the Elliott group and how the novel rearrangement of 1-acetyl-1-methylcyclohexa-2,5-diene was discovered. The proposed mechanism for the rearrangement is discussed which sets the stage for the work discussed in chapter 2. Chapter 2 presents a review of Birch reduction chemistry. This was utilised as a synthetic route to produce 1-acetyl-1-methylcyclohexa-2,5-diene which is used as the starting material for rearrangement reactions. Chapter 3 discusses the rearrangement reaction of 1-acetyl-1-methylcyclohexa-2,5-diene with a range of alkylating agents. It is followed by a computational study that evaluates the feasibility of the proposed mechanism. Chapter 4 describes the brief evaluation of Na-SG as a method for partial reduction of aromatic compounds.

Item Type: Thesis (MPhil)
Date Type: Submission
Status: Unpublished
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Date of First Compliant Deposit: 10 June 2016
Last Modified: 18 Jul 2017 01:30
URI: http://orca.cardiff.ac.uk/id/eprint/91722

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