The rearrangement of fatty cyclopropenoids in the presence of boron trifluoride |
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Authors: | Ian S. Gilkison Geoffrey G. Shone |
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Affiliation: | (1) Faculty of Science, Kingston University, KT1 2EE Kingston-upon-Thames, Surrey, England |
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Abstract: | The destruction of the cyclopropenoid ring system of methyl 9,10 methyleneoctadec-9-enoate (methyl sterculate) with boron trifluoride etherate has been shown to give a complex mixture of products, including methyl esters of C19 allenes (12%), a C18 alkyne (11%) and a variety of C19 and C20 conjugated dienes containing either a methyl or methylene branch. The methylene group lost from the methyl sterculate reactant in the formation of methyl octadec-9-ynoate is incorporated into a second molecule of reactant to yield a mixture of methyl 9-methylene-trans-nonadec-10-enoate and the 11-methylene-trans-9-isomer. |
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Keywords: | Alkynes carbon chain reduction and elongation cyclopropenoid ring opening dienes fatty cyclopropenoids Lewis acid rearrangement production of allenes sterculate sterculene |
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