Polystyrene-Bearing Cyclopentadienyl Metal Catalysts: Copolymerization of a Styrene Monomer Containing Cyclopentadiene Synthons

Article abstract of DOI:10.1021/ja00407a024

The reaction of p-styrylmagnesium bromide with norbornenone gave syn- and anti-7-hydroxy-7-(p-styryl)norborn-2-ene (6) which could be converted to either the syn- and anti-7-methoxy derivative (8) or anti-7-chloro-7-(p-styryl)norborn-2-ene (7).Both styryl monomers 7 and 8 were copolymerized with styrene and divinyl benzene to give polymers (9) containing 10 mol percent of 7-substituted norbornyl derivatives.Treatment of the 7-chloro polymer (9c,d) with butyllithium or reaction of uncross-linked 7-methoxy polymer (9a) with sodium-potassium alloy generated the polymer-attached cyclopentadienyl anion that could be converted to a polymer bound η⁵-cyclopentadienyldicarbonylrhodium catalyst (12).Quenching the polymer containing cyclopentadienyl anion gave a polymer containing cyclopentadiene units (11).This polymer could be converted to the polymer-bound η⁵-cyclopentadienyldicarbonylcobalt analogue (13).Although 13 was not a Fischer-Tropsch catalyst, 12 would effect the hydroformylation of 1-hexene and the reduction of aromatic substrates.