By F.G.A. Stone, Robert West (Eds.)
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Extra info for Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses
When the gas ratio was 2/1, the isomer ratio was still low and the competing hydrogenation and isomerization reactions were serious. However, conducting the reaction with a 100-fold molar excess of triphenylphosphine gave a slightly higher isomer ratio ( 5 . 6 ) and decreased the competing reactions to a combined 4-5%. In an "ultimate" reaction conducted in molten triphenylphosphine under 400 psi, high rates were obtained, as well as isomer ratios up to 16: 1, but the competing hydrogenation accounted for 7-2S% of the product composition.
1 Benzene solvent; PHz,80 atm. 2. Phosphine-ModiJied Catalysts The introduction of alkyl phosphine complexes of cobalt carbonyl as hydroformylation catalysts was reported to have a significant effect on product composition (50, 51). 0, catalyst [Co,(CO), + 2(n-C4H,),P]. Under the same conditions except at a temperature of 190°C, the n-hexanol was 84% of the hexyl alcohol produced. In addition to the increased proportion of linear product, other differences from the unmodified cobalt-catalyzed reaction may be noted.
77% Substitution on the double-bond carbon a to the oxygen increased the difficulty of the reaction, and formyl attachment occurred exclusively on the p-carbon [Eq. (42)]. Thus, these substituted olefins also followed the rule of Keulemans (49). ROY L. PRUETT 44 Rosenthal and co-workers (91, 92) studied the cobalt hydroformylation of various unsaturated carbohydrates. As with other a$-unsaturated ethers, addition of the formyl group occurred almost exclusively at the double-bond carbon (Y to the oxygen.
Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses by F.G.A. Stone, Robert West (Eds.)