178164-23-3Relevant academic research and scientific papers
1,4-Dimethyl-2,3-diphenylfulvene: A convenient precursor to heteroatom-substituted-1-methyl-2,5-dimethyl-3,4-diphenylcyclopentadienyl transition metal complexes
Donovalova, Jana,Jackson, Carl R.,Mintz, Eric A.
, p. 85 - 89 (2007/10/03)
Reaction of 2,5-dimethyl-3,4-diphenylcyclopent-2-enone (1) with Ph3P=CH2 in THF gave 2,5-dimethyl-3,4-diphenylcyclopent-2-ene-1-ylidene (2) in 75% yield. Treatment of 2 with one equivalent of Br2, followed by two equivalents of triethylamine gave 1,4-dimethyl-2,3-diphenylfulvene (3) in 60% overall yield. Treatment of 3 with LiCH3 and LiC6H5 followed by FeCl2 gave [η5-1-CH3CH2-2,5-(CH3)2-3,4-(C6H5)2C5]2Fe and [η5-1-C6H5CH2-2,5-(CH3)2-3,4-(C6H5)2C5]2Fe, respectively, in good yield. Treatment of 3 with LiNHC(CH3)3 and LiP(C6H5)2 followed by FeCl2 gave [η5-1-(CH3)3CNHCH2-2,5-(CH3)2-3,4-(C6H5)2C5]2Fe and [η5-1-(C6H5)2PCH2-2,5-(CH3)2-3,4-(C6H5)2C5]2Fe, respectively, in good yield. Treatment of 3 with (R)-LiNHCH(CH3)C6H5 followed by FeCl2 gave the corresponding enantiomerically pure ferrocene complex (R,R)-[η5-1-C6H5CH(CH3)NHCH2-2,5-(CH3)2-3,4-(C6H5)2C5]2Fe in 44% yield.
