Some reactions of methyl 12-mesyloxyoleate
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Methylricinoleate 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.
Thesis, MSc Master of Science
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