高等学校化学学报

高等学校化学学报 ›› 1992, Vol. 13 ›› Issue (9): 1206.

• 论文 • 上一篇    下一篇

有机磷化合物的研究(LVII)——二苯(氧)基氯膦对肟基的自由基加成——合成1-氨基取代三烷基氧化膦及烷基膦酸酯的新途径

袁承业1, 漆又毛1, 陈国飞1, 赵成学2   

  1. 1. 中国科学院上海有机化学研究所, 上海, 200032;
    2. 华中理工大学化学系, 武汉, 430074
  • 收稿日期:1991-07-07 修回日期:1992-05-24 出版日期:1992-09-24 发布日期:1992-09-24
  • 通讯作者: 袁承业

Studies on Organophosphorus Compounds (LVII)——Radical Addition of Diphenyl (Diphenoxy) Phosphorus Chloride to Oximes——A New Synthetic Approach to-1-Aminoalkyl-Diphenylphosphine Oxides and Diphenyl-1-Aminoalkylphosphonates

YUAN Cheng-Ye1, QI You-Mao1, CHEN Guo-Fei1, ZHAO Cheng-Xue2   

  1. 1. Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai, 200032;
    2. Huazhong University of Science and Technology, Department of Chemistry, Wuhan
  • Received:1991-07-07 Revised:1992-05-24 Online:1992-09-24 Published:1992-09-24

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摘要： 二苯基氯膦或二苯氧基氯膦对醛(酮)肟的反应可作为合成1-氨基烷基二苯基氧化膦或1-氨基烷基膦酸二苯酯的新方法,具有条件温和、操作方便及得率高的优点。EPR研究结果揭示了这类反应属自由基机理。

关键词: 二苯基氯膦, 二苯氧基氯瞵, 1-氨基取代三烷基氧化膦, 自由基加成, 顺磁共振谱

Abstract: The reaction of diphenyl(phenoxy) phosphorus chlorides with oximes in the presence of triethylamine in a perhalogenated solvent CFCl2CF2Cl can serve as a new synthetic approach to 1-aminoalkyl diphenyl phosphine oxides or diphenyl 1-aminoalkylphosphonates with good or excellent yields under mild conditions.Direct EPRobservations of radical intermediates Ph2＝O,PhCH＝N·originated from the homolytic scission of the unstable condensation product Ph2PON＝CHPh in the first stage,and the spin adduct of Ph2＝O to Ph2PON＝CH-Ph,has revealed the first example of radical addition of phosphorus reagents to  bonds.

Key words: Diphenylphosphorus chloride, Diphenoxyphosphorus chloride, 1-Aminoalkyl diphenylphosphine oxide, Radical addition, EPR

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