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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (16): 1885-1890. 上一篇    下一篇

研究论文

三种新型二苯砜氮杂环蕃N,N’-二对甲苯磺酰基-1,m-二氮杂[m.1]对环蕃-n-砜的合成与表征(m＝8,10,12; n＝15,17,19)

杨秉勤* 刘飞龙 白银娟 杨亚婷 张秉林

  

  1. (西北大学合成与天然功能分子化学教育部重点实验室 西安 710069)

  • 投稿日期:2008-12-30 修回日期:2009-03-25 发布日期:2009-08-28
  • 通讯作者: 杨秉勤

Synthesis and Characterization of Three Kinds of New Azaparacyclophane Sulfone N,N’-di(p-toluenesulfonyl)-1,m-diaza[m.1] paracyclophane-n-sulfone (m＝8,10,12; n＝15,17,19)

Yang, Bingqin* Liu, Feilong Bai, Yinjuan Yang, Yating Zhang, Binglin

  

  1. (Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Northwest University, Xi’an 710069)
  • Received:2008-12-30 Revised:2009-03-25 Published:2009-08-28
  • Contact: Yang, Bingqin

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以N,N’-二对甲苯磺酰基-4,4’-二氨基二苯砜与二溴代烷为原料, 高度稀释条件下合成了三种新型有硫原子桥连的氮杂环蕃N,N’-二对甲苯磺酰基-1,8-二氮杂[8.1]对环蕃-15-砜(C); N,N’-二对甲苯磺酰基-1,10-二氮杂[10.1]对环蕃-17-砜(D); N,N’-二对甲苯磺酰基-1,12-二氮杂[12.1]对环蕃-19-砜(E). 提供了三种环蕃化合物的合成方法. 用IR, 1H NMR和元素分析证实了新化合物结构. 分析了化合物D的单晶结构数据, 为环蕃化合物的空间结构研究提供了晶体学依据.

关键词: 二苯砜环蕃, 合成, 表征, 晶体结构

N,N’-Di(p-toluenesulfonyl)-1,8-diaza[8.1]paracyclophane-15-sulfone (C), N,N’-di(p-toluenesul- fonyl)-1,10-diaza[10.1]paracyclophane-17-sulfone (D) and N,N’-di(p-toluenesulfonyl)-1,12-diaza[12.1]- paracyclophane-19-sulfone (E) were synthesized under a high dilution condition by the cyclization between dibromide and N,N’-di(p-tosylamino)diphenylsulfone (B), which was prepared using 4,4’-diamino diphenyl sulfone and p-toluenesulfonyl chloride as raw materials. The structures were confirmed by IR, 1H NMR and elemental analysis. The crystal structure of compound D was determind, which can provide the basis for study of structures of cyclophane compounds.

Key words: azaparacyclophane, synthesis, characterization, crystal structure

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