The conversion of 1,1′-dibromoferrocene to 1,2-dibromoferrocene: The ferrocene-chemist's dream reaction

Inorganic Chemistry Communications

Volumn 11, Issue 1, 2008, Pages 15-19

  Butler, Ian R ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

Bromoferrocene; Ferrocene; Iron; Lithiation; Phosphine cycopentadienyl

Indexed keywords

EID: 37849001999     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2007.09.020     Document Type: Article

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64. 1,1′-Dibromoferrocene is readily obtained from 1,1′-dilithioferrocene or its tertiary amine adducts by quenching with dibromotetrafluoroethane, hexabromoethane or tetrabromoethane. Of these quenching reagents the first of these is the reagent of choice however its commercial availability is limited.
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67. Pertinent experimental data is given as Supplementary material.
68. In this case diiodotetrafluoroethane is the quenching reagent of choice although iodine is commonly used as a quenching reagent in similar reactions. Where a bulk preparation of 1,1′-diiodoferrocene (>50 g) is required the method using tin precursors [6] leads to clean products on economic grounds however where small sample are required (∼5 g) quenching 1,1′-dilithioferrocene with diiodotetrafluoroethane is the reagent of choice and indeed we have successfully used this method in our undergraduate laboratories for more than 10 years. An alternative synthesis via the boronic acid [22c] is also available for iodoferrocene which can itself serve as a direct precursor for the ortho-lithiation reaction. The ortho-lithation of di-iodoferrocene has also been carried out as an undergraduate class experiment at the University of Wales to prove its ease of synthesis.
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