Studies on Macrocyclic Acetylenic Compounds

McMaster, Denis (1970) Studies on Macrocyclic Acetylenic Compounds. PhD thesis, University of Glasgow.

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Section I In an attempt to synthesise compounds related to the as yet unknown 1,6-didehydro-[10]-annulene, intermolecular Castro type coupling of the cuprous salts of l-(o-iodophenyl)-2-propyn-1-ol and derivatives was investigated. Intermolecular coupling of derivatives suggested by model reactions was either unsuccessful, however, or gave a complex mixture, the nature of which could not be clarified. The synthesis of 'half-cyclised' compounds, formally only one stage away from the desired ten membered ring system was achieved, however, and some new examples of the Castro reaction, including some anomalies and failures, were discovered. Section II Intermoleeular Castro-type coupling of the cuprous salt of m-iodophenylacetylene was found to give a complex mixture, the major component of which was shown to be the 'cyclic pentamer' derived from five molecules of the cuprous salt. Evidence was obtained for the presence of similar cyclic compounds of lower and higher molecular weight. A series of compounds resulting from mixed oxidative and Castro-type coupling was also isolated from the reaction product.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1970
Depositing User: Enlighten Team
Unique ID: glathesis:1970-78550
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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