Abstract
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)(PPh 3) 3 and RhH(PPh 3) 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)(PPh 3) 3. RhH(CO)(PPh 3) 3 promotes ring-opening isomerization of 4-phenyl-1-methylenespiro[2,2]pentane to afford Rh[ η 3-anti-CH 2C{C( CH 2)Ph}CHCH 3](PPh 3) 2 ( 2) at 50 °C and Rh{ κ 1, η 2-CH 2CH(Ph)C( CH 2)CH CH 2}(CO)(PPh 3) 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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