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Davies, Leslie Stewart (1970) Rearrangements of quinolizinium-1-diazonium salts and related reactions. Doctoral thesis, Keele University.
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Abstract
The methods of synthesis and known properties of aminoquinolizinium compounds are reviewed.
A number of 1-aminoquinolizinium salts when treated
with aqueous nitrous acid undergo rearrangement. Investigation by degradation and synthesis showed the initial products are cis-3-(v-triazolo[l,S-a]pyridyl)acraldehydes. These are rapidly isomerised to the trans-isomers. The mechanism of the rearrangement is discussed and the synthesis and properties of other v-triazolo[l,5-a]pyridines are reviewed.
The thermal isomerisation and decomposition of
3-(v-triazolo[l,5-a]pyridyl)acraldehydes to 5-(2-pyridyl)pyrazoles is reported and a mechanism for the rearrangement is suggested.
In the last section the photochemistry of a,B-unsaturated carbonyl compounds is briefly reviewed. The photochemical conversion of some heterocyclic acraldehydes to derivatives of propionic acid is described. Some limitations of the reaction
are reported and a mechanism proposed, support for which is provided by studies on suitably deuterium labelled compounds.
Item Type: | Thesis (Doctoral) |
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Subjects: | Q Science > QD Chemistry |
Divisions: | Faculty of Natural Sciences > School of Chemical and Physical Sciences |
Depositing User: | Lisa Bailey |
Date Deposited: | 11 Feb 2019 12:22 |
Last Modified: | 11 Feb 2019 12:22 |
URI: | https://eprints.keele.ac.uk/id/eprint/5802 |