By F.G.A. Stone, Robert West (Eds.)
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Additional resources for Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses
Another pertinent observation is the fact that the reaction proceeded twice as fast in n-butyraldehyde (polar) as in benzene (nonpolar), even though the catalyst concentration was reduced to only one-third the comparable level. A graphic illustration of this effect is given in Fig. 9. The rate of gas uptake is plotted as a function of time for a reaction conducted in benzene and again for a second reaction conducted in butyraldehyde. The rate of reaction in the polar solvent was initially fast and decreased with time.
Org. Chem. 34, 327 (1969). Copyright by the American Chemical Society. 25 Hydroformylation T A B L E XI11 HYDROFORMYLATION OF 1-OCTENE WITH VARIOUS Hz/CO RATIOS"(5'9) RhiC (g) Reaction time (min) % Aldehyde which H,/CO Ratio Iil 311 113 15 10 10 30 30 60 86 90 75 is straight-chain 'I Octene, 112 g ; 5% RhlC. 10-15 g; toluene, 200 ml; triphenyl phosphite, 15 g; temperature. 90°C; pressure, 80-100 psi. addition to affording improved isomer ratios, the reaction proceeded under conditions of temperature which were much milder than those effective with cobalt or even phosphine-modified cobalt catalysts.
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. High yields of product were obtained, but hydrogenation to alcohol was facile, even under mild conditions, as noted in Eq. (43): By careful control of reaction conditions, modest yields of the intermediate aldehyde could be obtained. E.
Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses by F.G.A. Stone, Robert West (Eds.)