Using Hydrazine to Link Ferrocene with Re(CO)3: A Modular Approach

J Organomet Chem. 2016 Sep 1:818:145-153. doi: 10.1016/j.jorganchem.2016.06.004. Epub 2016 Jun 7.

Abstract

Acetyl ferrocene and diacetyl ferrocene both readily react with an excess of hydrazine to afford the corresponding hydrazone compounds. These compounds can then be linked to Re(CO)3 via a metal-mediated Schiff base reaction, resulting in a series of ferrocene-Re(CO)3 conjugates with different stoichiometries. Conjugates with 1:1, 1:2, and 2:1 ferrocene: Re(CO)3 ratios can be produced via this "modular" type synthesis approach. Several examples of these conjugates were structurally characterized, and their spectroscopic, electrochemical, and spectroelectrochemical behaviors were investigated. The electronic structures of these compounds were also probed using DFT and TDDFT calculations.

Keywords: Ferrocene; Schiff base conjugate; density functional theory; electrochemistry; tricarbonyl rhenium(I).