SCHEDULED MAINTENANCE
Displacement of the hydroxy-group from ferrocenylmethanol by amines
Abstract
The reaction of ferrocenylmethanol with piperidine, t-butylamine, cyclohexylamine, or benzylamine to afford the appropriately substituted ferrocenylmethylamine proceeds efficiently in dilute aqueous acetic acid. The reaction with piperidine in aqueous solution is very slow outside the pH range 4–7. Aniline, p-nitroaniline, p-anisidine, and urea effect nucleophilic substitution of ferrocenylmethanol in the absence of acetic acid. The mechanism is discussed and evidence is presented that in this reaction aniline is a more effective nucleophile than piperidine.
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