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)
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: http://eprints.keele.ac.uk/id/eprint/5802

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