Reactions of 1-amino-n′-ferrocenemethylcarboxylate with electrophiles: A combined synthetic, electrochemical, and theoretical study

The reactivity of 1-amino-n′-ferrocenemethylcarboxylate, 1,n′-H2N-Fc-COOCH3 (2) toward alkylating agents is reported and MeNH-Fc-COOMe (3), EtNH-Fc-COOMe (4), EtSCH2CH2NH-Fc-COOMe (5), (EtO)2P(O)NH-Fc-COOMe (6) are synthesized by reacting 2 with MeI, EtI, EtSCH2CH2Cl and (CN)(EtO)2P(O), respectively. Cyclic voltammetry of these compounds shows different half-wave potential characteristics compared to aminoferrocene and is dependent on the nature of the substituents, which is rationalized by molecular orbital calculations.