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Title: 1-alkoxyvinyl esters as synthetic intermediates
Author: Thomas, John Anthony Griffiths
Awarding Body: Keele University
Current Institution: Keele University
Date of Award: 1968
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The chemistry and properties of 1-alkoxyvinyl esters and of cyclopropanones are reviewed. A number of 1-ethoxyvinyl esters have been isolated, both for their intrinsic interest and also because of their value as synthetic intermediates. Phthaloyl and 4-nitrophthaloyl derivatives of amino-acid esters have been prepared by reaction of phthalic acid or 4-nitrophthalic acid with ethoxyacetylene (without isolation of the correspondinc di-1-ethoxyviny: esters), in the presence of the corresponding amino-acid ester hydrochloride, Reaction of maleic acid and succinic acid with ethoxyacetylene under the same conditions, however, has yielded only the corresponding maleamic or succinamic acid. l-Ethoxy-2-ethoxycarbonylcyclopropyl carboxylates (2-ethoxy-carbonylcyclopropanone acylals) have been prepared by the thermal deconposition of ethyl diazoacetate, catalysed by anhydrous copper sulphate, in the presence of an excess of the corresponding 1-ethoxyvinyl ester. When 1-ethoxyvinyl thiolacetate was used in this reaction, however, the product was a nitrogen containing compound, to which a pyrazoline structure has been tentatively assigned. Experiments with 1-ethoxyvinyl esters, methylene di-iodide and zinc-copper couple yielded products which could not be successfully purified Conversion of the 2-ethoxycarbonylcyclopropanone acylals to 2-ethoxycarbonylcyclopropanone was attempted using a variety of conditions. However, in every case, only products arising from ring cleavage reactions were obtained. An interesting boron trifluoride-catalysed rearrangnent to the corresponding acyl (or aroyl) succinic acid ester was observed.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry