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Title: Bridged bicyclic compounds
Author: Kean, Norman Buchanan
ISNI:       0000 0001 3596 0018
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1973
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This thesis is concerned with certain aspects of the application of Bredt's Rule in bridged bicyclic compounds. The reported monodecarboxylation of bicyclo[2,2,2]-octane-2,5-dione-1,4-dicarboxylic acid (1) to give bicyclo-[2,2,2]octane-2,5-dione-l-carboxylic acid (2) has been found to be genuine, and the structure of the product has been confirmed by synthesis. Bicyclo[2,2,2]octan-2-one-1-carboxylic acid (3) has also been prepared, and (2) and (3) have been shown to be resistant to decarboxylation. The decarboxylation of (1) has been found to proceed with racemisation, and conclusions have been drawn concern- ing the mechanism of the reaction. The Cope elimination has been shown to be unsatisfactory in generating the strained alkene bicyclo[2,2,2]oct-1-ene. Two synthetic approaches to bicyclo[4,3,1]decane-2,9-dione, a key intermediate for the study of isomeric "anti-Bredt" alkenes, were unsuccessful, as were attempts to prepare a derivative of the [5]-metacyclophane system.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available