St Andrews Research Repository

St Andrews University Home
View Item 
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  • Register / Login
JavaScript is disabled for your browser. Some features of this site may not work without it.

1, 2, 4 - triazines and 1, 2, 4, 5 - tetrazines as monomers for Diels-Alder polymerisations

Thumbnail
View/Open
MichaelBruceMPhilthesis1995_original_C.pdf (11.74Mb)
Date
1995
Author
Bruce, Michael John
Supervisor
Smith, D. M.
Metadata
Show full item record
Abstract
Chapter 1 (Introduction) comprises a brief overview of the origins, mechanism and scope of the Diels-Alder reaction. It deals with the three different Diels Alder reaction types and highlights the utilisation of the reaction in general terms for the synthesis of aromatic and heteroaromatic ring systems. Particular attention has been paid to the inverse electron-demand Diels-Alder reactions of nitrogen-containing heterocycles, where aromatisation is brought about by the thermodynamically-driven loss of molecular nitrogen, leading to both carbocyclic and heterocyclic ring systems. Chapter 2 (Results and Discussion) develops the ideas formed in Chapter 1 to seek possible bis-dienes and bis-dienophiles for utilisation in polymer synthesis. Attention has been concentrated on possible routes to bis-l,2,4-triazines and 1,2,4,5- tetrazines, which are novel compounds, and on their possible use in both inter- and intra-molecular Diels-Alder reactions. A new method for the synthesis of bis-glyoxals involving the oxidation of the corresponding diacetyl-aromatics using HBr/DMSO is the most reliable and is capable of being scaled up without safety/environmental problems. The bis-glyoxals are then readily convertible into 5,5'-linked bis-l,2,4-triazines which are potential bis-dienes for Diels-Alder reactions. The attempted intermolecular reactions of the bis-triazines with a range of diethynyl-aromatics have, however, proved unsuccessful so far. Attempts to form bis-(o-ethynylphenols) for intramolecular Diels-Alder reactions after coupling to bis-triazines have also been unsuccessful. Several 5-(substituted phenyl)-1,2,4-triazines have also been formed, with the intention of coupling these through the phenyl substituent to a central difunctional core. Several 1,2,4,5-tetrazines have been formed with similar intent. Chapter 3 (Experimental) details the synthetic procedures and the Bibliography follows.
Type
Thesis, MPhil Master of Philosophy
Collections
  • Chemistry Theses
URI
http://hdl.handle.net/10023/22571

Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.

Advanced Search

Browse

All of RepositoryCommunities & CollectionsBy Issue DateNamesTitlesSubjectsClassificationTypeFunderThis CollectionBy Issue DateNamesTitlesSubjectsClassificationTypeFunder

My Account

Login

Open Access

To find out how you can benefit from open access to research, see our library web pages and Open Access blog. For open access help contact: openaccess@st-andrews.ac.uk.

Accessibility

Read our Accessibility statement.

How to submit research papers

The full text of research papers can be submitted to the repository via Pure, the University's research information system. For help see our guide: How to deposit in Pure.

Electronic thesis deposit

Help with deposit.

Repository help

For repository help contact: Digital-Repository@st-andrews.ac.uk.

Give Feedback

Cookie policy

This site may use cookies. Please see Terms and Conditions.

Usage statistics

COUNTER-compliant statistics on downloads from the repository are available from the IRUS-UK Service. Contact us for information.

© University of St Andrews Library

University of St Andrews is a charity registered in Scotland, No SC013532.

  • Facebook
  • Twitter