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The rearrangement of fatty cyclopropenoids in the presence of boron trifluoride

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Journal of the American Oil Chemists’ Society

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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Authors and Affiliations

  1. Faculty of Science, Kingston University, KT1 2EE, Kingston-upon-Thames, Surrey, England

    Ian S. Gilkison & Geoffrey G. Shone

Authors
  1. Ian S. Gilkison
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  2. Geoffrey G. Shone
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Gilkison, I.S., Shone, G.G. The rearrangement of fatty cyclopropenoids in the presence of boron trifluoride. J Am Oil Chem Soc 70, 607–612 (1993). https://doi.org/10.1007/BF02545328

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  • DOI: https://doi.org/10.1007/BF02545328

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