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Norborn-5-ene-( N,N -dipyrid-2-yl)carbamide ( M1 ) was copolymerized with  exo,exo -[2-(3-ethoxycarbonyl-7-oxabicyclo[2.2.1]hept-5-en-2-carbonyloxy)ethyl]trimethylammonium iodide ( M2 ) using the Schrock catalyst Mo( N -2,6-Me 2 -C 6 H 3 )(CHCMe 2 Ph)(OCMe(CF 3 ) 2 ) 2   [Mo]  to yield poly( M1 - b - M2 ). In water, poly( M1 - b - M2 ) forms micelles with a critical micelle-forming concentration (cmc) of 2.8 × 10 −6  mol L −1 ; Reaction of poly( M1 - b - M2 ) with [Rh(COD)Cl] 2  (COD = cycloocta-1,5-diene) yields the Rh(I)-loaded block copolymer poly( M1 - b - M2 ) -Rh  containing 18 mg of Rh(I)/g of block copolymer with a cmc of 2.2 × 10 −6  mol L −1 . The Rh-loaded polymer was used for the hydroformylation of 1-octene under micellar conditions. The data obtained were compared to those obtained with a monomeric analogue, i.e. CH 3 CON(Py) 2 RhCl(COD) ( C1 , Py = 2-pyridyl). Using the polymer-supported catalyst under micellar conditions, a significant increase in selectivity, i.e. an increase in the  n : iso  ratio was accomplished, which could be further enhanced by the addition of excess ligand, e.g., triphenylphosphite. Special features of the micellar catalytic set up are discussed.

beilstein journal of organic chemistry

Ring opening metathesis polymerization-derived block copolymers bearing chelating ligands: synthesis, metal immobilization and use in hydroformylation under micellar conditions