51985-23-0

Upstream product

• 16643-55-3 2,5-dimethyl-3,4-diphenyl-2-cyclopentene-1-one 

Downstream Products

• 178164-23-3 1,1'-bis-t-butylaminomethyl-2,2',5,5'-tetramethyl-3,3',4,4'-tetraphenylferrocene 
• 178164-22-2 1,1'-dibenzyl-2,2',5,5'-tetramethyl-3,3',4,4'-tetraphenylferrocene 
• 160211-74-5 1,1'-diethyl-2,2',5,5'-tetramethyl-3,3',4,4'-tetraphenylferrocene 
• 178164-25-5 1,1'-bis-diphenylphosphinomethyl-2,2',5,5'-tetramethyl-3,3',4,4'-tetraphenylferrocene 

Relevant 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

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.