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dc.contributor.advisorGunstone, F. D.en
dc.contributor.authorSaid, Ahmed Ahbeilen
dc.coverage.spatial165 pen
dc.date.accessioned2021-04-08T08:45:35Z
dc.date.available2021-04-08T08:45:35Z
dc.date.issued1970
dc.identifier.urihttps://hdl.handle.net/10023/21806
dc.description.abstractMethylricinoleate contains a homoallylic hydroxy group and is therefore a potential source of homoallylic carbonium ions which can undergo an interesting rearrangement and furnish cyclopropane compounds. This thesis reports a study of the reaction of methyl 12-mesyloxyoleate, the mesyloxy group being a better leaving than a hydroxy group. Reactions carried out in methanol, acetic acid, and aqueous acetonitrile, in the presence of a suitable buffer to control the pH, gave interesting methoxy, acetoxy, and hydroxy cyclopropajse esters. In the absence of buffer the solution becomes acidic and the major product is the trans isomer of methyl 12-methoxy (acetoxy, hydroxy) octadecenoates. The substituted cyclopropane esters are very reactive and undergo rearrangement reactions. In other solvents (dimethylsulphoxide, acetonitrile, triglyme) sodium methoxide promotes an elimination reaction giving mixtures of conjugated and non-conjugated methyl octadecadienoates.en
dc.language.isoenen
dc.publisherUniversity of St Andrewsen
dc.subject.lccQD305.A2S2
dc.subject.lcshFatty acidsen
dc.titleSome reactions of methyl 12-mesyloxyoleateen
dc.typeThesisen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnameMSc Master of Scienceen
dc.publisher.institutionThe University of St Andrewsen


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