Single Electron Transfer Reactions of Enamines with Polyfluoroalkyl Iodides──Novel Synthesis of α-Polyfluoroalkyl Ketones and Aldehydes

Chem. J. Chinese Universities ›› 1996, Vol. 17 ›› Issue (6): 896.

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Single Electron Transfer Reactions of Enamines with Polyfluoroalkyl Iodides──Novel Synthesis of α-Polyfluoroalkyl Ketones and Aldehydes

HE Hai-Ying¹, ZHAO Cheng-Xue¹, WENG Zhong-Yuan¹, BAI Ling-Jun², LIAO Ren-An²

1. Department of Chemistry, Huazhong University of Science and Technology, Wuhan 430074;
2. National Laboratory of Elemental organic Chemistry Nankai University, Tianjin

Received:1995-06-02 Online:1996-06-24 Published:1996-06-24

Abstract

Abstract: Fairly high yields of α-polyfluoroalkyl ketones(aldehydes) formed in the reactions of enamines with polyfluoroalkyl iodides were characterized by UV,IR,MS,¹H NMR,¹⁹F NMRand elemental analysis,The electron transfer in nature of these reactions was proved by spin trapping and inhibition experiments.The addition of catalytic amounts of SmI₂ has significantly shortened the reaction time and increased the yields of α-polyfluoroalkyl ketones.

Key words: Enamine, Polyfluoroalkyl iodide, Samarium diiodide, Polyfluoroalkylation, Electron transfer

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HE Hai-Ying, ZHAO Cheng-Xue, WENG Zhong-Yuan, BAI Ling-Jun, LIAO Ren-An. Single Electron Transfer Reactions of Enamines with Polyfluoroalkyl Iodides──Novel Synthesis of α-Polyfluoroalkyl Ketones and Aldehydes[J]. Chem. J. Chinese Universities, 1996, 17(6): 896.

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Single Electron Transfer Reactions of Enamines with Polyfluoroalkyl Iodides──Novel Synthesis of α-Polyfluoroalkyl Ketones and Aldehydes

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