Study on the Mechanism of Reduction of 9- Fluorenylidenemalononitrile with NaBH4

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (07): 1095-1099. Previous Articles Next Articles

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硼氢化钠还原9-亚芴基丙二腈的反应机理研究

冯乙巳^1,2，张博¹，杨春燕¹，许华建*^,1,2

(¹合肥工业大学化学工程学院合肥 230009)
(²可控化学与材料化工安徽省重点实验室合肥 230009)

收稿日期:2010-12-29 修回日期:2011-01-27 发布日期:2011-02-18
通讯作者: 许华建 E-mail:hjxu@hfut.edu.cn

Study on the Mechanism of Reduction of 9- Fluorenylidenemalononitrile with NaBH₄

Feng Yisi^1,2 Zhang Bo¹ Yang Chun-yang¹ Xu Huajian*^,1,2

(¹School of Chemical and Engineering, Hefei University of Technology, Hefei 230009)
(²Anhui Key Laboratory of Controllable Chemistry Reaction & Material Chemical En-gineering, Hefei 230009)

Received:2010-12-29 Revised:2011-01-27 Published:2011-02-18
Contact: XU Hua-Jian E-mail:hjxu@hfut.edu.cn

The reduction of 9-fluorenylidenemalononitrile (FDCN) by NaBH₄ in oxygen-free and saturated oxygen condition was studied respectively in this paper. The results showed that electron transfer can occur and α-carbon-anion produced firstly in the reaction system. In oxygen-free condition, the proton attacked α-carbon-anion to generate the corresponding reduction product. In the CH₃CN-CH₃OD mixed solvent, the yield of major product 9-d-FDCNH was improved on prolonging the reaction time or increasing reaction temperature. In saturated oxygen solution, the generation of oxidation product 9-fluorenone (FDO) was due to the incoordinate hydride transfer mechanism. In other words, electron transfer was slightly faster than hydrogen atom transfer.

Key words: NaBH₄, FDCN, reduction reaction, electron transfer

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FENG Yi-Si, ZHANG Bo, YANG Chun-Yan, XU Hua-Jian. Study on the Mechanism of Reduction of 9- Fluorenylidenemalononitrile with NaBH₄[J]. Chin. J. Org. Chem., 2011, 31(07): 1095-1099.

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硼氢化钠还原9-亚芴基丙二腈的反应机理研究

Study on the Mechanism of Reduction of 9- Fluorenylidenemalononitrile with NaBH₄

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