By F.G.A. Stone, Robert West (Eds.)
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Extra resources for Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses
Higher temperatures promote the isomerization and cause the percentage of a-carboethoxypropionaldehyde to decrease. Higher pressures of carbon monoxide inhibit the isomerization and result in increased percentages of the a-isomer. High pressures of hydrogen favor the hydrogenation and would thus tend to promote hydrogenation of the initially formed branched-chain intermediate before isomerization could occur. 04 mol%; pressure, loo0 atm 1/1 HJCO. 35 Hydroformylation HZ CH,CHCOOC,H, I 1 CH,CHCOOC,H, I Hz CH,CH,COOC,H, I CH,CH,COOC,H, I CORh(CO),,4 CHO (12) In the hydroformylation of crotonate esters, three different aldehydes may be formed, denoted as the a-,p-, or y-isomers: CH,CH=CHCOOR + CO + H, + CH,CH,CHCOOR a CHO + CH,CHCH,COOR p (32) I CHO + CH,CH,CH,COOR y I CHO The cobalt-catalyzed reaction was studied by isolation of the lactones formed by hydrogenation and lactonization at higher temperatures (73).
Res. Dev. 8,291 (1969). Copyright by the American Chemical Society. Thus, the rule of Keulemans (49), that a-quaternary carbon formyl compounds are not formed, was followed. The olefin isomerized to allow formyl attachment to a primary carbon atom. Addition of phosphine, which decreases isomerization. resulted in no reaction. B. Cyclic Olefins Differences in reactivity have been exhibited between acyclic and different types of cyclic olefins. Vinylcyclohexene in a cobalt hydroformylation at 120"-134°C and 475-720 atm pressure gave a 65% yield of a mixture of mono- and dialdehydes (66).
Falbe and Huppes (70) reported that the cobalt hydroformylation of ethyl acrylate at 300 atm and 140°C gave >90% yield of the p-isomer (10). which was hydrogenated at temperatures of 200"-250"C. The final product was a lactone, as shown in Eq. (30). CH,=CHCOOC,H, + CO + H, c o (CO) [OHCCH,CH,COOC,H,] I H, (0 Lo 1 200°-250"C [ HOCH,CH,CH,COOC,H,] 7 (30) ROY L. 04 mol%; temperature, 80°C. The products of the rhodium-catalyzed hydroformylation were responsive to the reaction temperatures and, to a lesser degree, to the reaction pressure, as shown in Tables XXI-XXII.