Synthesis and Reactions of Bridged Bicyclic Compounds

Young, Graham Andrew Reid (1971) Synthesis and Reactions of Bridged Bicyclic Compounds. PhD thesis, University of Glasgow.

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The research described in this thesis is devoted to synthetic and mechanistic studies in bridged bicyclic systems. The thesis is divided into three parts:- Part I: The Total Synthesis of Racemic Guaiol. The plant sesquiterpene guaiol has been synthesised in racemic form, from laevulinic acid and 2-methylcyclopentanon'e via an intermediate, l-methyltricyclo-(6,2,1,0 2,6)-undec-2 6-en-5,11-dione. Bridge fission of this diketone yields a hydroazulene enone-ester which has been elaborated to guaiol. Part II: The Acid Catalysed Cleavage of Bicyclo-(3,2,1)-oct-2-en-8-one. Although bicyclo-(3,2,1)-oct-2-en-8-one derivatives cleave in acidic solution to cycloheptene carboxylic acid derivatives, the corresponding alcohols do not fragment under similar circumstances. The corresponding syn alcohol undergoes a facile transannular cyclisation when treated with bromine. A similar transannular cyclisation occurs when the ketone is treated with bromine in an alcoholic solvent. Part III: A Re-investigation of the Reduction and Hydrolysis of Unsaturated Medium Ring Gem-Diesters. The previously reported base-catalysed transannular cyclisation of unsaturated medium ring gem-diesters has been re-investigated. In contrast to these earlier findings, the hydrolysis and reduction of these diesters proceed in the normal manner.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1971
Depositing User: Enlighten Team
Unique ID: glathesis:1971-78558
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 30 Jan 2020 15:10
Last Modified: 30 Jan 2020 15:10

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