Unsymmetrically disubstituted ferrocenes. Part IV. The synthesis and reactivity of 2-(NN-dimethylaminomethyl)ferroceneboronic acid

Abstract

The reaction of lithiated (NN-dimethylaminomethyl)ferrocene with tri-n-butyl borate has given [2-(NN-dimethyl-aminomethyl)ferroceneboronic acid. This amino-acid has been converted into the corresponding 2-chloro-,2-bromo-, and 2-iodo-(dimethylaminomethyl)ferrocenes. The methiodides of these halo-amines underwent nucleophilic displacement reactions with amines, phenol, and aqueous sodium hydroxide to afford a variety of 2-halo-ferrocenes.