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

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...

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Bibliographic Details
Published in:Lipids 2004-06, Vol.39 (6), p.583-587
Main Authors: Jie, M.S.F.L.K, Lam, C.N.W
Format: Article
Language:English
Subjects:
Boranes - chemistry
Boron
chemical reactions
epoxidation
Epoxy Compounds - chemistry
Esters - chemistry
Linoleic Acids, Conjugated - chemistry
Molecular Structure
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Summary: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.
ISSN:0024-4201
1558-9307
DOI:10.1007/s11745-004-1267-6