Abstract
The hydroformylation of camphene in the presence of platinum(II)/tin(II)/phosphine (diphosphine) catalytic systems with various achiral and chiral P-donor ligands has been studied. The reaction occurs regio-specifically to give exclusively the linear isomer of the corresponding aldehyde. With triphenylphosphine and chelating achiral diphosphines, i.e. 1,2-bis(diphenylphosphino) ethane, 1,3-bis(diphenylphosphino) propane and 1,4-bis(diphenylphosphino) butane, the chemoselectivity for hydroformylation of 90–96% and diastereoisomeric excess (d.e.) of the exo isomeric aldehyde of 16–30% have been achieved. The highest d.e. of 60% has been shown by the platinum/tin/( R)- or ( S)-BINAP system (BINAP—2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) with ca. 90% chemoselectivity for hydroformylation products at ca. 90% camphene conversion. A new aldehyde derived from α-fenchene, which could result from the skeletal isomerization of camphene under the reaction conditions has been detected (up to 30%) at the elevated tin/platinum ratio.
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