Synthesis and electrochemical properties of ferrocene-containing N-allylcarbamates: Structure of CH2CHCH2–NHCOO–CH2Fc
摘要:
A series of ferrocene-containing N-allylcarbamates, CH2=-CHCH2-NHCOO-(CH2)(m)Fc 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 CH2- Cl-2/0.1 M (NBu4PF6)-Bu-n utilising a glassy carbon working electrode. The ferrocenyl group showed reversible electrochemistry with the formal reduction potential (E degrees' 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, P2(1)/c space group) explained the good through bond communication that was electrochemically detected between the electron-withdrawing NHCOO group and electron-donating Fc modalities. (C) 2013 Elsevier Ltd. All rights reserved.