New PDF release: Advances in Organometallic Chemistry, Vol. 17: Catalysis and
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
However, a$-unsaturated esters may be hydroformylated smoothly. Acrylates and methacrylates have been the subject of considerable investigation. 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).
Results obtained with hexenoic acid esters are outlined in Table XXIV. With cobalt catalysts, hydroformylation of ethyl cinnamate gave 9 1% of the hydrogenation product ethyl hydrocinnamate (15) and only 8% of the expected lactone, 16 (72). However, rhodium catalysis was effective in directing the reaction in favor of hydroformylation (70). The comparative results obtained with cobalt and rhodium are outlined in Table xxv. (16) The simplest a,@-unsaturatedaldehyde, acrolein, gives nearly quantitative yields of the hydrogenation product propionaldehyde under hydroformylation conditions.
This ligand was used with rhodium to effect hydroformylation. The product solution was extracted with aqueous acid to transfer both metal catalyst and ligand to the aqueous phase. 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.
Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses by F.G.A. Stone, Robert West (Eds.)