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The redox behaviour of ferrocenyl alcohols and ferrocenediyl-diols: crystal and molecular structure of ferrocenyl(2-furyl) phenylmethanol

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Abstract

Cyclic voltammetry and controlled-potential coulometry show that ferrocenyl alcohols of type (C5H5)Fe(C5H4)C(OH)RR′ and ferrocenediols of type Fe[(C5H4)CCR′(OH)]2 undergo quantitative and reversible one-electron oxidation at the metal centre, and that the redox potentials are controlled predominantly by the inductive effects of the substituents at the α-carbon. The crystal structure of the new alcohol ferrocenyl(2-furyl)phenylmethanol not only confirms its molecular constitution, but also demonstrates that in the solid state it forms centrosymmetric hydrogen-bonded dimers involving cyclic (OH)2 bridge without any participation of the furan oxygen atom in the hydrogen bonding.

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  • Cited by (17)

    • From ferrocenyl selenoesters to diferrocenyl methanols

      2018, Journal of Organometallic Chemistry
      Citation Excerpt :

      During the electrochemical investigations of the diferrocenyl methanol compounds 4a and 4b two reversible well-separated one-electron redox processes could be detected for the ferrocenyl substituents with a redox separation of ΔE0’ = 330 mV (4a) and 367 mV (4b) (Table 3 and Fig. 6). This indicates a better stabilization of the positive charge within the diferrocenyl methanol systems in presence of a more electron-rich substituent with increased aromaticity at the aliphatic carbon atom [39,47,48]. Similar observations were made during the electrochemical study of diferrocenyl methanol in comparison with its aryl and alkyl functionalized derivatives [39,47,48].

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    Part IX of the series “The redox behaviour of ferrocene molecules”. For Part VIII, see Ref. [1].

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