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

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These substrates respond most dramatically to variations in reaction conditions with cobalt and with rhodium catalysis; both a- and p-isomers may be obtained in very high specificity. y Hs CH,=C-COOCH, + CO + yH3 CH,C-COC€H3 H,- + I CHO (Y FH3 CH,-CH-COOCH3 I C HO ( 29) -isomer 0 -isomer (9) (10) One of the most interesting observations is that the a-isomer (9) contains a quaternary carbon atom attached to the formyl group, which is a violation of the rule of Keulemans (49). It must be that electronic effects are dominant for this type of substrate, particularly when the effects of phosphine-modified rhodium systems are considered (vide infra).

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. The halide complex RhCl(CO)(PPh,), was effective as a catalyst at temperatures >60°C and pressures of CO/H, > 20 atm (24). However, with such halide complexes an inhibition period was always observed which could be eliminated by addition of a base such as triethylamine.

The percent of n-aldehyde rose rapidly as the carbon monoxide partial pressure was increased up to 30-40 atm CO; further increase had little effect. 1-Pentene clearly gave a higher percentage of straight-chain aldehyde than 2-pentene, but the difference was insignificant in the lower P c o experiments. The hydrogen partial pressure has a small but reproducible effect on the hydroformylation product composition. The direction of the change found was the same as for carbon monoxide partial pressures: the experiments gave higher percentages of n-aldehyde.

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