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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (05): 623-628. 上一篇    下一篇

研究论文

6-烷氧基乙氧/硫基-6-氧/硫-双苯并[1,3,2]-二氧磷杂八环的合成与波谱特征

张晓梅a,b，王道全a，陈万义*,a   

  1. (a中国农业大学应用化学系 北京 100094)
    (b安徽理工大学化工系 淮南 232001)
  • 收稿日期:2006-04-14 修回日期:2006-08-25 发布日期:2007-05-10
  • 通讯作者: 陈万义

Synthesis and Spectral Characteristics of 6-O/S-Alkoxyethyl- 12H-[1,3,2]dioxaphosphocin-6-oxides/sulfides

ZHANG Xiao-Meia,b, WANG Dao-Quana, CHEN Wan-Yi*,b   

  1. (a Department of Applied Chemistry, China Agricultural University, Bei-jing100094)
    (b Department of Chemistry and Engineering, University of Science and Tech-nology, Huainan 232001)
  • Received:2006-04-14 Revised:2006-08-25 Published:2007-05-10
  • Contact: CHEN Wan-Yi

PDF

1109

被引次数

12

通过双(3,5-二氯-2-羟基-苯基)甲烷(1)分别与POCl3或PSCl3在三乙胺存在下关环, 再与单烷氧基乙醇钠作用, 得到了新化合物5或6; 以1与P4S10及三乙胺关环的产物4与烷氧基溴乙烷反应得到了7. 测试了5, 6和7的1H, 13C和31P NMR及MS数据, 并讨论了其特征. 观察到了磷与C1H (C11H)或C3H (C9H)与P的5JPH偶合常数(约为0.9 Hz). 在1与POCl3关环产物与单甲氧基乙醇反应的产物中, 分离到了一个副产物8并确定了它的化学结构. 1与POCl3按3∶2的物质的量比在三乙胺存在下反应, 得到收率75%的8.

关键词: 合成, 核磁共振, 质谱, 6-烷氧基乙氧/硫基-6-氧/硫-双苯并[1,3,2]-二氧磷杂八环

From bis(3,5-dichloro-2-hydrxy-phenyl)methane (1), the new [1,3,2] dioxaphosphocins 5, 6 and 7 were synthesized. 1 reacted with POCl3 or PSCl3 to give cyclic compound 2 or 3, which reacted with monoalkyl-1,2-ethandiol to offer 5 or 6. 7 was prepared by the reaction of 1 with P4S10 in the presence of triethylamine, and then reacted with 2-alkoxyl ethyl bromide. The 1H, 13C and 31P NMR and MS spec-tra of the new compounds were evaluated and discussed. The coupling 5JPH (about 0.9 Hz) of P and C1H or C3H was observed in the first time. A solid compound 8 was separated from the crude product 5 and its structure was determined. When 1 and POCl3 reacted at the molar ratio of 3∶2, 8 was obtained in yield of 70%.

Key words: synthesis, NMR, MS, [1,3,2]dioxaphosphocin-6-oxides/sulfide