Synthesis and electrochemical properties of ferrocene-containing N-allylcarbamates: Structure of CH2CHCH2–NHCOO–CH2Fc

A series of ferrocene-containing N-allylcarbamates, CH2CHCH2–NHCOO–(CH2)mFc with m = 1–4 and Fc = ferrocenyl, was synthesized by reacting allylisocyanate with different ferrocenylalcohols, Fc–(CH2)n–OH (n = 1–4). The electrochemistry of the carbamates was studied by cyclic voltammetry in CH2Cl2/0.1 M NnBu4PF6 utilising a glassy carbon working electrode. The ferrocenyl group showed reversible electrochemistry with the formal reduction potential (Eo′ versus FcH/FcH+) of the ferrocenyl group inversely proportional to spacer chain length. The single crystal X-ray structure of the complex with m = 1 (monoclinic, P21/c space group) explained the good through bond communication that was electrochemically detected between the electron-withdrawing NHCOO group and electron-donating Fc modalities.

Ferrocene-containing N-allylcarbamates Fc–(CH2)m–OOCHN–CH2CHCH2 with m = 1, 2, 3 or 4 have been synthesised, studied electrochemically and the single crystal structure of the m = 1 derivative has been solved.Figure optionsDownload as PowerPoint slide