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Title: Rearrangements of quinolizinium-1-diazonium salts and related reactions
Author: Davies, Leslie Stewart
Awarding Body: Keele University
Current Institution: Keele University
Date of Award: 1970
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry