高等学校化学学报

高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (S1): 486.

• Synthetic Sciences • 上一篇    下一篇

Solid-state Synthesis of Aryl and Vinyl of Ferrocene Derivatives via Wittig Reaction

LIU Wan-Yi2, XU Qi-Hai1, LIANG Yong-Min1, MA Yong-Xiang1   

  1. 1. National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000;
    2. Key Laboratory of Energy Chemistry Technology and Applied Organic Chemistry, Ningxia University, Ningxia 750021
  • 出版日期:2000-12-31 发布日期:2000-12-31

Solid-state Synthesis of Aryl and Vinyl of Ferrocene Derivatives via Wittig Reaction

LIU Wan-Yi2, XU Qi-Hai1, LIANG Yong-Min1, MA Yong-Xiang1   

  1. 1. National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000;
    2. Key Laboratory of Energy Chemistry Technology and Applied Organic Chemistry, Ningxia University, Ningxia 750021
  • Online:2000-12-31 Published:2000-12-31

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摘要：

Organometallic structure possessing extensively conjugated π-electron system are an interesting class of potentially highly nonlinear molecular blocks and photoactive semiconductor[1,2]. The title compounds were synthesized following Wittig reaction or palladium-catalyzed reaction of olefines and iodoferrocene, which proceed in solution and refluxing[3]. However, there are always some disadvantages such as long reaction time, difficult work-up and low yield. Herein we report a free-solvent synthesis of aryl and vinyl ferrocene derivatives. As shown in the table, the phosphoning salt (1mol),NaOH (1.5mol) and formylferrocene (1mol) were mixed by grinding at room temperature to 65℃ in dry state to give the corresponding title compounds in 60-90% yield. The reaction was usually completed within a few minutes. The product thus obtained is mainly E-isomer. It could be emphasized that solid-state Wittig reaction is fast, cleaner and efficient.

Abstract:

Organometallic structure possessing extensively conjugated π-electron system are an interesting class of potentially highly nonlinear molecular blocks and photoactive semiconductor[1,2]. The title compounds were synthesized following Wittig reaction or palladium-catalyzed reaction of olefines and iodoferrocene, which proceed in solution and refluxing[3]. However, there are always some disadvantages such as long reaction time, difficult work-up and low yield. Herein we report a free-solvent synthesis of aryl and vinyl ferrocene derivatives. As shown in the table, the phosphoning salt (1mol),NaOH (1.5mol) and formylferrocene (1mol) were mixed by grinding at room temperature to 65℃ in dry state to give the corresponding title compounds in 60-90% yield. The reaction was usually completed within a few minutes. The product thus obtained is mainly E-isomer. It could be emphasized that solid-state Wittig reaction is fast, cleaner and efficient.

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