Reaction of Ferrocenecarbaldehyde with O-phenylenediamine
Crystal structure of N-ferrocenylmethyl-2-ferrocenyl-benzimidazole
The reaction of ferrocenecarbaldehyde with o-phenylenediamine in the presence of p-toluenesulphonic acid results in the synthesis of N-ferrocenylmethyl-2-ferrocenyl-benzimidazole, 1, and 2-ferrocenyl-benzimidazole, 2. The molecular structure of 1 has been determined by single crystal X-ray analysis. It crystallises in the triclinic system, space group P1, a = 10.069(7), b = 13.625(8), c = 9.314(7) A ̊, α = 92.75(5)°, β = 104.68(6)°, γ = 95.43(6)°; V = 1227(1) A ̊ 3, Z = 2. An electrochemical study of 1 and 2 dichloromethane: methanol (10:1) has been carried out. 2 shows a reversible oxidation processes at Ep a = 535 mV. The addition of HCl (1 equiv.) switches the oxidation potential giving a new wave at Ep a = 800 mV. 1 shows a reversible 2e - oxidation processes at Ep a = 558 mV which is split into two different waves when 1 equiv. of HCl is added. The switching process is reversible for 1 and 2 and addition of base (KOH) leads to the former oxidation potential. © 1995.
A. Benito et al., "Reaction of Ferrocenecarbaldehyde with O-phenylenediamine," Journal of Organometallic Chemistry, Elsevier, Jan 1995.
The definitive version is available at http://dx.doi.org/10.1016/0022-328X(95)05583-B
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