Ferrocene has two structure 1 and 2.It is bonded to an aromatic ion cyclopentadienyl anion.Aromatic species such as benzene , cyclopentadienyl anion undergo electrophilic aromtic substitutions.

Then,will Ferrocene undergo electrophilic aromtic substitution ?

Which conformer between 1 and 2, would preferentially undergo friedel crafts acylation reaction?

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1 Answer 1


Due to the aromatic character of the cyclopentadienyl ligands, ferrocene can undergo electrophilic aromatic substitution reactions typical of aromatic compounds such as benzene. Ferrocene shows very high reactivity towards electrophiles, making it more closely comparable to phenol than to benzene, references and examples here and here.

  • $\begingroup$ This does not answer weather conformer 2 or conformer 1 is more reactive towards acylation..In my question i have already mentioned that cyclopentadienyl anion is aromatic.So cyclopentadienyl does undergo electrophillic aromatic substitution. $\endgroup$ May 26, 2019 at 8:55
  • 1
    $\begingroup$ Ferrocene is formed from two planar cyclopentadienyl rings, not anions. The two rings are staggered with respect to each other, but are otherwise equivalent so there is no answer to your question. $\endgroup$
    – Waylander
    May 26, 2019 at 9:02

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