高等学校化学学报

高等学校化学学报 ›› 1996, Vol. 17 ›› Issue (6): 896.

• 论文 • 上一篇    下一篇

烯胺和含氟碘烷的单电子转移反应──α-氟烷基酮、醛的合成

贺海鹰1, 赵成学1, 翁中原1, 白令君2, 瘳仁安2   

  1. 1. 华中理工大学化学系, 武汉 430074;
    2. 南开大学元素有机化学国家重点实验室
  • 收稿日期:1995-06-02 出版日期:1996-06-24 发布日期:1996-06-24
  • 通讯作者: 赵成学
  • 作者简介:贺海鹰,男,26岁,博士研究生.
  • 基金资助:

    南开大学元素有机化学国家重点实验室基金

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. 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

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摘要： 由多氟烷基碘化物对烯胺的氟烷基化反应,合成了6种α-氟烷基酮和3种α-氟烷基醛并完成了它们的UV、IR、MS、1HNMR和(19)FNMR结构鉴定及元素分析。通过活泼中间体的自旋截捕和抑制实验,揭示了本反应的单电子转移机理并发现SmI2的四氢呋喃溶液可催化本反应,使反应时间缩短、含氟酮产率提高。

关键词: 烯胺, 多氟烷基碘化物, 二碘化钐, 氟烷基化, 单电子转移反应

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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