Summary
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1.
Ferrocene enters into a hydrogen exchange reaction with various acids, deuterosulfuric, hydrochloric enriched with deuterium, deuterophosphoric acid, trichloracetic and glacial acetic acid solution, and trifluoracetic.
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2.
In the reaction between deuterosulfuric acid and ferrocene, the hydrogen exchange occurs at a higher rate than the oxidation of ferrocene to ferricinium cation. The ferricinium cation does not enter into hydrogen exchange with acids.
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3.
From studies made on the hydrogen exchange kinetics of ferrocene, acetyl ferrocene, diacetyl ferrocene, and toluene in benzene solution with trichloracetic acid, the exchange rate of ferrocene is greater by a factor of 1000 than the exchange rate of acetyl ferrocene and greater by a factor of 2000 than that of diacetyl ferrocene. Under these conditions, benzene does not enter into the hydrogen exchange reaction, while toluene exchanges at a rate three order of magnitude slower than ferrocene.
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4.
From the kinetic data on hydrogen exchange, the compounds investigated may be arranged in the following series in order of decreasing electrophilic substitution power: ferrocene-acetyl ferrocene-diacetyl ferrocenetoluene.
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Nesmeyanov, A.N., Kyrsanov, D.N., Setkina, V.N. et al. A study of hydrogen exchange in nonbenzoid (surocene) aromatic systems. Russ Chem Bull 11, 1845–1848 (1962). https://doi.org/10.1007/BF00921336
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DOI: https://doi.org/10.1007/BF00921336