By F.G.A. Stone, Robert West (Eds.)
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Additional info for Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses
Fell and Rupilius (95) found that a rhodium tributylphosphine catalyst Hydroformy lation 45 was effective for the partial bishydroformylation of butadiene. 7 mol% of R,P were employed. The active catalyst was preformed by heating the mixture to 150°C for 30 minutes. After a reaction period of 3 hours, 8090% yields of hydroformylation products were obtained, which consisted of 58 mot% C, monoaldehydes and 42 mol% C, dialdehydes. The composition of the C, fraction was 96% ti-valeraldehyde. The composition of the C, dialdehyde fraction was as follows: 58% 2 methyl- 1 ,5-pentanediol; 29% 2-ethyl-l,4-butanediol; 9% 1 -6-hexanediol; and 4% not identified.
Prod. 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).
These are understood as factors that influence the equilibrium between phosphine and carbonyl complexes. For amine resins, an additional implication was the fact that partial reduction of aldehyde to alcohol occurred and further changed the solvent polarity. Some pertinent data are summarized in Table XXXII. 25 20 25 65 80 Substrate, I-hexene; temperature, 100°C; pressure, 1000-2000 psi 2/1 H,/ co.
Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses by F.G.A. Stone, Robert West (Eds.)