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
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.
To which the formyl group is attached. I = a,I1 = p. etc. " Tri-wbutylphosphine. ' Tricyclohexylphosphine. c 38 ROY L. 5 P-Phenyl-y-butyrolactone. * Ethyl hydrocinnamate. initially formed compounds underwent further hydrogenolysis and condensation reactions. Rhodium oxide also catalyzed the hydroformylation of the diethyl acetal at 100°C and 200 atm. The products were the n- and isoaldehyde formed in a 1 :2 ratio, respectively. However, when the diacetate of acrolein was the substrate and benzene the solvent, rhodium catalysis resulted in the formation of 2-methyl-3-acetoxyacrolein and acetic acid as the only isolable products: CH,=CHCH(OCOCH,), + CO + H, - [CH,~HCH(OCOCH,),] cHo CH,COOH 1 + (36) CH C-CHOCOCH, ,ICHO The cobalt-catalyzed hydroformylation of acrolein diacetate in ethanol proceeded in a complicated fashion.
The catalyst was then regenerated by neutralization and extraction with organic solvents. Hydroformylation 47 In another study (102), a triarylphosphine with a sulfonyl group on each phenyl was prepared and used with rhodium in a buffered aqueous system. The hydroformylation of propylene was conducted at 80°C and 50 atm of synthesis gas. 7 : I . In rhodium hydroformylations. highly efficient separation and recovery of catalyst becomes imperative, because of the very expensive nature of the catalyst.
Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses by F.G.A. Stone, Robert West (Eds.)