The hydroformylation of two isomeric arylalkenes, 1-(4'-methoxy-phenyl)- propene and 3-(4'-methoxy-phenyl)-propene was investigated in the presence of in situ rhodium and platinum catalysts. While α- and β-substituted formyl regioisomers were formed in the hydroformylation of propenylarene type substrate by rhodium catalysts, all three regioisomers were isolated in platinum-catalyzed reactions. Very high chemoselectivities (> 99%) were obtained in the first case. The accompanying hydrogenation of the substrate took place to a very small extent. Due to isomerization of the terminal double bond lower chemoselectivities and the formation of chiral 2-(4'- methoxy)-butanal were observed with 3-(4'-methoxyphenyl)-propene as substrate. E.e.'s up to 7.5% and 27.5% were obtained for 2-(4'-methoxy)- butanal in asymmetric hydroformylation of 1-(4'-methoxy-phenyl)-propene by rhodium-diop catalyst and in the hydroformylation of 3-(4'-methoxy-phenyl)- propene by platinum-tin(II)chloride catalyst, respectively.
- Platinum- phosphine-tin(II)chloride catalyst
- Rhodium-phosphine catalyst
ASJC Scopus subject areas
- Process Chemistry and Technology
- Physical and Theoretical Chemistry