Ring-opening isomerization of methylenecyclopropanes catalyzed by hydridorhodium(I) complexes

Add time:09/09/2019    Source:sciencedirect.com

2-Phenyl-1-methylenecyclopropane is isomerized into 2-phenyl-1,3-butadiene and 1-phenyl-1,3-butadiene in the presence of catalytic amounts of RhH(CO)(PPh3)3 and RhH(PPh3)4. The Rh-containing product of the reactions has a 2-phenyl-1-methylallyl (or 1-phenyl-1-methylallyl) ligand, and is formed also from the reaction of 2-phenyl-1,3-butadiene with RhH(CO)(PPh3)3. RhH(CO)(PPh3)3 promotes ring-opening isomerization of 4-phenyl-1-methylenespiro[2,2]pentane to afford Rh[η3-anti-CH2C{C(CH2)Ph}CHCH3](PPh3)2 (2) at 50 °C and Rh{κ1,η2-CH2CH(Ph)C(CH2)CHCH2}(CO)(PPh3)2 (3) at −35 °C. X-ray crystallography of 2 shows the π-allylic ligand having a methyl group at anti position. The mechanism for formation of 2 via intermediate 3 is discussed.

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