[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=O.[CH-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl.C1CCCCC1>[C:2]([C:3]1[CH2:4][CH2:5][CH2:6][C:7]=1[C-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1)(=[O:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]6-Oxo-6-phenylhexanoyl chloride (9.0g; 0.04 mole) and ferrocene (7.44g; 0.04 mole) in methylene chloride (150 ml) were stirred at 0° and aluminium chloride (5.34g; 0.04 mole) was added over 40 minutes at 0°. The mixture was stirred at 0° (2 hr), and then at room temperature (90 min). More aluminium chloride (4g; 0.03 mole) was added and the reaction mixture was heated under reflux for 90 minutes. Water was added, the organic layer run off, and the aqueous layer extracted with methylene chloride (100 ml). The combined organic layers were washed with water (3 × 200 ml), and dried (sodium sulphate) to yield a brown oil. The portion of this oil which was insoluble in hot cyclohexane was discarded and the remainder (2.7g) was subjected to preparative thin layer chromatography to yield 2.1g (15%) of pure 1-benzoyl-2-ferrocenylcyclopentene as a brown solid mp 136°-137°.
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