Synthesis, electrochemical properties and fungicidal activity of 1,1′-bis(aroyl)ferrocenes and their derivatives

• Published in: Applied organometallic chemistry Vol. 22; no. 1; pp. 25 - 29
• Main Authors: Dou, Yan-Ye, Xie, Yun-Fu, Tang, Liang-Fu
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.01.2008
• Subjects: bioorganometallic chemistry; electrochemical property; ferrocene; fungicidal activity
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.1345

Reaction of functionalized cyclopentadienyl sodium CH3O2CArC(O)CpNa (Ar = aryl and Cp = cyclopentadienyl) with FeCl2 in a 2:1 ratio gives 1,1′‐bis(aroyl)ferrocenes [CH3O2CArC(O)Cp]2Fe in reasonable yields. Upon treatment of these aroyl compounds with NaBH4, the ketone carbonyl is reduced to yield compounds [CH3O2CArCH(OH)Cp]2Fe, while with the stronger reductive reagent LiAlH4, diols [HOCH2ArCH(OH)Cp]2Fe are obtained. All new compounds were characterized by IR and NMR spectroscopic analyses. Their electrochemical behavior was investigated by cyclic voltammetry. The structure of [CH3O2CC10H6C(O)Cp]2Fe was further confirmed by single crystal X‐ray diffraction analysis. In addition, the fungicidal activities of these new compounds were also determined in vitro. Copyright © 2007 John Wiley & Sons, Ltd. A series of 1,1′‐bis(aroyl)ferrocenes and their derivatives were synthesized, and their electrochemical behavior as well as fungicidal activity investigated.