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Journal of Coordination Chemistry Volume 63, 2010 - Issue 11
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Original Articles

Synthesis, structure, and fungicidal activity of thia- and aza-ferrocenophanes

Yun-Fu Xie Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China
,
Yan-Ye Dou Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China
,
Shan-Shan Chen Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China
,
Na Mi Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China
&
Liang-Fu Tang Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. ChinaCorrespondence[email protected]
Pages 1904-1912 | Received 13 Jan 2010, Accepted 03 Mar 2010, Published online: 14 Jun 2010
 
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Abstract

Reaction of bridging dicyclopentadienyl disodium E(CH2COCpNa)2 (E = S or NPh, Cp = cyclopentadienyl) with FeCl2 yields thia- and aza-[5]ferrocenophanes E(CH2COCp)2Fe [E = S (1) and NPh (2)]. Treatment of C14H8(CH2SCH2COCpNa)2 (C14H8 = 9,10-anthracenyl) with FeCl2 affords dithia-[12]ferrocenophane C14H8(CH2SCH2COCp)2Fe (3), while similar reaction of C6H4(CH2SCH2COCpNa)2 (C6H4 = 1,4-phenyl) with FeCl2 provides a mixture of dithia-[12]ferrocenophane C6H4(CH2SCH2COCp)2Fe (4) and tetrathia-[12,12]ferrocenophane [C6H4(CH2SCH2COCp)2Fe]2 (5), which are separated easily by column chromatography. These five compounds were characterized by IR and NMR spectroscopic analyses and the structures of 2 and 3 were further confirmed by single crystal X-ray diffraction. The electrochemical behaviors of 1–4 were investigated by cyclic voltammetry. In addition, their fungicidal activities against Alternaria solani, Cercospora arachidicola, Physalospora piricola, and Botrytis cinerea were tested in vitro.

Acknowledgment

This work is supported by the National Natural Science Foundation of China (no. 20721062).

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