Aspects of Bicyclo (3,3,1) Nonane Chemistry

Stevenson, James Ronald (1969) Aspects of Bicyclo (3,3,1) Nonane Chemistry. PhD thesis, University of Glasgow.

Abstract

SECTION I: A study of the solvolytic behaviour of exo- and endo-1,5-dimethylbicyclo (3,3,1) nonan-9-one-2-yl tosylates revealed a stereochemical control in product formation which can best be explained in terms of ion-pair intermediates. Evidence for an acyl migration during solvolysis was found. SECTION II: A 2,6-hydride shift was discovered during the deuteration of exo-2-hydroxybicyclo (3,3,1) nonan-6-one. Studies of other possible 2,6-interactions in the bicyclo (3,3,1) skeleton, (i. e. homoenolisation between C2 and C6, synthesis of twistane derivatives from 2,6-disubstituted bicyclo (3,3,1) nonane compounds and reactivity of 6-hydroxy-2-cations) were also initiated. Finally the influence of a keto group at C6 and C9 on the solvolytic rate constant of the epimeric-2-tosylates was also studied and evidence found to support the current ideas regarding the influence of polar groups on ionisation of tosylates.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1969
• Depositing User: Enlighten Team
• Unique ID: glathesis:1969-78527
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2020 15:12
• Last Modified: 30 Jan 2020 15:12
• URI: https://theses.gla.ac.uk/id/eprint/78527