Synthesis and Characterization of Homoannularly Disubstituted and Heteroannularly Trisubstituted Ferrocene Derivatives by Arsenic and Silicon or by Arsenic and Tin

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• 作者：Hongguang Du ; Ki Chul Park ; Feng Wang ; Shuming Wang ; Qun Liu ; Shiwei Zhang ; Yuli Huang ; Shujian Shi
• 刊名：Organometallics
• 出版年：2007
• 出版时间：December 3, 2007
• 年：2007
• 卷：26
• 期：25
• 页码：6219 - 6224
• 全文大小：98K
• 年卷期：v.26,no.25(December 3, 2007)
• ISSN：1520-6041

文摘

The ferrocene derivatives (5-10) homoannularly disubstituted and heteroannularly trisubstituted bytwo different kinds of main-group elements, i.e., arsenic (As) and silicon (Si) or tin (Sn), were synthesizedfrom N,N-dimethylaminomethylferrocene (1) and its diphenylarsino derivative 2 through mono- ordilithiation, followed by substitution with the organo-substituted chlorides R_mMCl_n [R = alkyl, (m, n) =(2, 2) or (3, 1)] of main-group elements M = As, Si, or Sn. The dimethylaminomethyl (-CH₂NMe₂)group of the starting compounds facilitates lithiation of the cyclopentadienyl (Cp) ring and introduceslithium into the ortho-position of the -CH₂NMe₂ groups by the directing functionality. The efficiencyof the subsequent substitution reaction with the organo-substituted chlorides R_mMCl_n is influenced notonly by their reactivity but also by the spatial factors of the main-group elements and the ferrocenederivative molecules to be reacted. All products 5-10 were identified by elemental analysis, protonnuclear magnetic resonance (¹H NMR) spectroscopy, and mass spectrometry (MS). Furthermore, theX-ray crystal structure of 5 was determined. The application of 5, 6, and 10 to fungicides for crop plantdiseases was examined. The results of the percent inhibition test for fungal growth have indicated thatthe derivative 10 has high fungicidal activity for early tomato blight.