Volume 39, Issue 6 p. 583-587
Article

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

Marcel S. F. Lie Ken Jie

Corresponding Author

Marcel S. F. Lie Ken Jie

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

To whom correspondence should be addressed at Department of Chemistry, The University of Hong Kong, Pokfulam Rd., Hong Kong, SAR, China. E-mail: [email protected]Search for more papers by this author
Corey N. W. Lam

Corey N. W. Lam

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

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First published: 01 June 2004
Citations: 4

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.