Conjugation of polyunsaturated fats: Methyl linoleate with tris(triphenylphosphine) chlororhodium
1971
DeJarlais, W.J. | Gast, L.E.
Tris(triphenylphosphine) chlororhodium in methanol produces nearly 95% conjugated dienes from methyl linoleate. The dienes are principally cis,trans - and cis,cis-conjugated. Since deuterium is introduced into the products when deuterated methanol is the solvent, a dihydride complex is the probable intermediate. The reaction is sluggish in chloroform, possible because the dihydride cannot easily form. The catalyst is activated in chloroform with hydrogen. Since no reduction occurs in the absence of hydrogen, hydrogenation likely occurs by hydrogenolysis of the alkyl complex of the dihydride olefin rather than a transfer of both hydrogens from the hydride complex.
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