✦ LIBER ✦

Fatty acids, part 21: ring opening reactions of synthetic and natural furanoid fatty esters

✍ Scribed by M.S.F. Lie Ken Jie; S. Sinha

Publisher: Elsevier Science
Year: 1981
Tongue: English
Weight: 408 KB
Volume: 28
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(81)90038-4

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✦ Synopsis

Methyl 2,5-disubstituted C~8 furanoid fatty ester (viz. methyl 9,12-epoxyoctadeca-9,11dienoate) was readily converted to methyl 9,12-dioxostearate using mineral or maleic acid. Conversion of the naturally occurring 2,3,5-trisubstituted furanoid fatty ester (viz. methyl 10,13-epoxy-11 -methyloctadeca-10,12-dienoate) to the corresponding methyl 10,13-dioxo-11methylstearate was much slower in rate under similar reaction conditions. The ease of separating the dioxo derivatives from a mixture of other common fatty esters was demonstrated and the cyclodehydration of the isolated dioxo derivatives to the parent furanoid ester was rapidly achieved using dilute BF3-methanol complex.

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