✦ LIBER ✦

Synthesis and physical properties of some unsaturated and hydroxy alkylseleno fatty acid derivatives

✍ Scribed by S.F. Marcel; Lie Ken Jie; Y.K. Cheung

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 557 KB
Volume: 75
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(94)02404-s

No coin nor oath required. For personal study only.

✦ Synopsis

Three unsaturated 12-alkylseleno (alkyl = Me, Et, Pr) C18 derivatives were prepared by reaction of sodium alkylselenide with the tosyloxy derivative of methyl ricinoleate. Reaction of sodium alkylselenide (alkyl = Me, Et, Pr, hexyl) or phenylselenide with methyl 10,11-epoxyundecanoate gave the corresponding ethyl 10-hydroxy-ll-alkyl-(phenyl)seleno-undecanoates. The IH-NMR spectroscopic analysis revealed strong hydrogen-bonding between the selenium atom and the hydroxy function. Acid-catalyzed dehydration of methyl 10-hydroxy-li-methylselenoundecanoate gave methyl 10-undecenoate as the major product, due to neighboring participation reaction of the selenium atom in the aikyl chain. To demonstrate the stability of unsaturated selenium-containing fatty acid analogues, the total synthesis of methyl 1 l-methyl-seleno-9-cis-undecenoate was elaborated.

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