Bridged Bicyclic Compounds

Kean, Norman Buchanan (1973) Bridged Bicyclic Compounds. PhD thesis, University of Glasgow.

Abstract

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.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1973
• Depositing User: Enlighten Team
• Unique ID: glathesis:1973-78633
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 28 Feb 2020 12:09
• Last Modified: 28 Feb 2020 12:09
• URI: https://theses.gla.ac.uk/id/eprint/78633