Synthetic Approaches to Tricyclic Compounds

Taylor, Robert (1971) Synthetic Approaches to Tricyclic Compounds. PhD thesis, University of Glasgow.

Abstract

Synthetic routes to the tricyclo(5,3,1,1 2,6)dodecane and tricyclo(5,1,0,0 3,5)octane systems have been investigated. Routes to the former class have involved double Michael additions to 4,4'-dimethoxycyclohexa-2,5-dienone, and attempted preparation of a bis delta-enol-lactone from diethyl succinylsuccinate, but no tricyclic compounds were produced. Since approaches to the latter system, involving carbene additions to 3,3',6,6'-tetramethoxycyclohexa-1,4-diene gave a novel rearrangement to hydroquinone dimethyl ether, 1,2,4-trimethoxy benzene and a pentamethoxy biphenyl, the tricyclo(5,1,0,0,3,5)octan-2,6-dione has been synthesised by reaction of 4,4'-dimethoxycyclohexa-2,5-dienone with an ylid reagent. A reported violation of Bredt's rule involving monodecarboxylation of bicyclo(2,2,2)octan-2,5-dione-1,4-dicarboxylic acid to bicyclo(2,2,2)octan-2,5-dione-1-carboxylic acid has been proved genuine, but the other expected decarboxylation product, bicyclo(2,2,2)octan-2,5-dione has not been detected.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1971
• Depositing User: Enlighten Team
• Unique ID: glathesis:1971-78572
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2020 15:10
• Last Modified: 30 Jan 2020 15:10
• URI: https://theses.gla.ac.uk/id/eprint/78572