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Fatty acids : XI. The synthesis of epoxides from methyl octadecadienoates and a study of their chromatographic properties by M.S.F. Lie Ken Jie; C.H. Lam is a Chemistry article available to read on EtoBox.

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Tetrahydrofuranyl and tetrahydropyranyl epoxides of the isomers of methyi octadecanoate have been prepared by the oxymercuration-demercuration reaction of dimethy!ene-interrupted methyl cis,cis-octadecadienoates. The thin-layer chromato-Opraphy (on silica gel and silica1 gel impregnated with silver nitrate) and gas-Iiquid chromatography (on OV-101 and Silar 10C phases) of the derivatives have been studied. The mass spectra of these compounds are also reported\_ Oxymercuration-demercuration reactions of dienes and unsaturated alcohols to yield diofs, tetrahydrofurans and tetrahydropyrans are well documented2s3. Gunstone and IngJk" have extended this reaction to enable the rapid identification of certain unsaturated long-chain alcohols. In an earlier study we reported the result of the oxymercuration-demercuration reactions of methyl undecenoates, undecynoates and some diunsatnrated Cl8 fatty ester$. In order to further our study of the chemical properties of the dirnethyIeneinterrupted methyl c&c&octadecadieqoates?, we have prepared all of the positional isomers of the tetrahydrokranyl ('FHF) (I), and all except one of the tetrahydropyranyl (THP) (2), derivatives from this unique se

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Author

M.S.F. Lie Ken Jie; C.H. Lam

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 1873-3778)

Published

1976

Language

EN

Field

Chemistry (Physical Sciences)