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Reaction of mono-epoxidized conjugated linoleic acid ester with boron trifluoride etherate complex

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Lipids

Abstract

The reaction of methyl 11, 12-E-epoxy-9Z-octadecenoate (1) with boron trifluoride etherate furnished a mixture of methyl 12-oxo-10E-octadecenoate (3a) and methyl 11-oxo-9E-octadecenoate (3b) in 66% yield. Methyl 9, 10-Z-epoxy-11 E-octadecenoate (2) with boron trifluoride etherate furnished a mixture of methyl 9-oxo-10 E-octadecenoate (4a, 45%) and methyl 10-oxo-11 E-octadecenoate (4b, 19%). A plausible mechanism is proposed for these reactions, which involves the attack on the epoxy ring system by BF3, followed by deprotonation, oxo formation, and double bond migration to give a mixture of two positional α,β-unsaturated C18 enone ester derivatives (3a/3b, 4a/4b). The structures of these C18 enone ester derivatives (3a/3b, 4a/4b) were identified by a combination of NMR spectroscopic and mass spectrometric analyses.

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Abbreviations

TMS:

tetramethylsilane

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Authors and Affiliations

  1. Department of Chemistry, The University of Hong Kong, Pokfulam Rd., Hong Kong, SAR, China

    Marcel S. F. Lie Ken Jie & Corey N. W. Lam

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  1. Marcel S. F. Lie Ken Jie
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  2. Corey N. W. Lam
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Correspondence to Marcel S. F. Lie Ken Jie.

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Jie, M.S.F.L.K., Lam, C.N.W. Reaction of mono-epoxidized conjugated linoleic acid ester with boron trifluoride etherate complex. Lipids 39, 583–587 (2004). https://doi.org/10.1007/s11745-004-1267-6

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  • DOI: https://doi.org/10.1007/s11745-004-1267-6

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