Cyclisation Reactions, Photochemistry and 13-C NMR of 9-Thiabicyclo [3,3,1] Nonanes

Nelson, Charles Russell (1977) Cyclisation Reactions, Photochemistry and 13-C NMR of 9-Thiabicyclo [3,3,1] Nonanes. PhD thesis, University of Glasgow.

Abstract

Both O- and C-acylated products have been isolated from the acid-catalysed acylations of 9-thiabicyclo [3,3,1] ndnan-2,6-dione with acid anhydrides. In particular, high acid concentration favours C-acylation with intramolecular aldol condensation of the initially formed products producing derivatives of 2-thiaadamantane. Structural assignment of these products was achieved by examining their chemical reactivity and by the application of a new C double resonance technique to elucidate their complex proton spectra. Acylations with acid halides were found to give inferior yields of both O- and C-acylated products. Photolytic sulphur extrusion from diketones and bisenones of the 9-thiabicyclo [3,3,1] nonane series and the related 9-oxides and 9,9-dioxides has been investigated. Selected derivatives of 9-thiabicyclo[3,3,1]nonane and 9-thiabicyclo[3,3,1] non-2-ene were synthesised and tested for fungicidal, insecticidal and pharmaceutical activity.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1977
• Depositing User: Enlighten Team
• Unique ID: glathesis:1977-78759
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2020 14:56
• Last Modified: 30 Jan 2020 14:56
• URI: https://theses.gla.ac.uk/id/eprint/78759