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有机化学
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有机化学 ›› 1996, Vol. 16 ›› Issue (1): 23-28. 上一篇    下一篇

研究论文

联苯型[11], [14]和[17]环系氮杂支链套索冠醚的合成

刘刚;牛长荣;吴成泰   

  1. 湖南怀化师范高等专科学校化学系;武汉大学化学系
  • 发布日期:1996-02-25

Studies on synthesis of new biphenyl 11, 14 and 17-membered ring N-pivot lariat crown ethers

LIU GANG;NIU CHANGRONG;WU CHENGTAI   

  • Published:1996-02-25

被引次数

7

以碳酸钾为缩合剂, 2,2'-二羟基联苯分别与二对甲苯磺酸酯Ⅱa~c, Ⅳb,Ⅵb反应合成尚未见文献报道的联苯型单氮杂冠醚(1~3), 二氮杂冠醚9和11。3,9和11分别用氢溴酸去对甲苯磺酰基得到亚胺型氮杂冠醚4, 10和12。4与溴代烃RBr(R=-(CH2)3CH3, -CH2CH=CH2, -(CH2)7CH3, -(CH2)2O(CH2)2OC4H9)反应分别合成[11]环系氮支套索冠醚(5~8), 12与正溴丁烷反应合成[17]环系氮支冠醚13。以上13种化合物皆为新型未见文献报道, 其结构皆经元素分析, IR, ^1H NMR,MS确证。

关键词: 冠醚, 元素分析, 质谱法, 二甲苯磺酸酯, 联苯 P, 核磁共振谱法, 碳酸钾

New diphenyl 11-membered ring aza crown ethers (1~3), 14 and 17- membered ring diazacrown ethers (9, 11) were prepared by one step reaction of 2,2'-dihydroxydephenyl with compounds TsO(CH2CH2N)m(CH2CH2O)nCH2CH2NCH2TH2OTs(Ⅱa: m=n=0, R=C6H5-; Ⅱb:m=n=0, R=p-CH3C6H4; Ⅱc:m=n=0, R=Ts; Ⅳb:m=1, n=0, R=Ts; Ⅵb:m=n=1, R=Ts; Ts=tosyl) in DMF at 100~110℃, using anhydrous patassium carbonate as condensing agent. The tosyl groups of 3, 9 and 11 were removed by treatment with 40% HBr in ACOH in the presence of a large amount of phenol. Three new azacrown ethers 4, 10 and 12 were formed from 3, 9 and 11 respectively. New N-pivot lariat crown ethers 5~8 and 13 were prepared by one step reaction of 4 and 12 with RBr in CH3Cn at reflux temperature, using anhydrous K2CO3 as condensing ageny. They were characterized by elemental analysis, IR, ^1H NMR and MS.

Key words: ELEMENTAL ANALYSIS, MASS SPECTROGRAPHY, CROWN ETHER, NMR SPECTROMETRY, DIPHENYL P, POTASSIUM CARBONATE

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