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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (03): 310-313. 上一篇    下一篇

研究论文

含卤素端基的单取代对-叔丁基杯[6]芳烃的合成与表征

张春雷，曹蓓，龚淑玲，陈远荫*   

  1. (武汉大学化学与分子科学学院 武汉 430072)
  • 收稿日期:2005-06-01 修回日期:2005-09-06 发布日期:2006-02-28
  • 通讯作者: 陈远荫

Sytheses and Characterization of Mono-substituted p-tert-Calix[6]arenes and Their Derivatives

ZHANG Chun-Lei,CAO Bei,GONG Shu-Ling,CHEN Yuan-Yin*   

  1. (College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072)
  • Received:2005-06-01 Revised:2005-09-06 Published:2006-02-28
  • Contact: CHEN Yuan-Yin

PDF

1276

被引次数

9

用THF作为反应溶剂, K2CO3作碱, 对-叔丁基杯[6]芳烃与二溴丁烷、二溴己烷和1,4-二氯丁炔-2反应以中等产率选择性地合成了含有卤素端基的单取代对-叔丁基杯[6]芳烃2a～2c. 2a和2b可与对甲苯磺酸甲酯(MeOTs)反应高产率地得到全甲基化产物3a和3b. 通过核磁共振谱(1H NMR)和质谱(FAB-MS)表征, 发现所有化合物都具有预期结构, 2a～2c和3b在室温下是锥式构象, 而3a没有固定构象.

关键词: 单功能化, 甲基化, 构象, 杯[6]芳烃

Three mono-substituted p-tert-calix[6]arenes (2a～2c) with terminal halogen groups have been synthesized by treating p-tert-calix[6]arene with Br(CH2)4Br, Br(CH2)6Br or ClCH2C≡CCH2Cl in THF using K2CO3 as base in moderate yield, respec-tively. 2a and 2b could be further converted to 3a and 3b in high yields by MeOTs. Their structures and conformations were characterized by 1H NMR and MS spectra. It was concluded that 2a～2c and 3b existed in cone conformation at room temperature, but no confined conformation of 3a was observed.

Key words: methylation, conformation, mono-functionalization, p-tert-calix[6]arene