| Synthesis and nitration of calix[4] (aza)crowns |
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| 作者姓名： | 郑企雨 陈传峰 黄志镗 |
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| 作者单位： | Institute of Chemistry，Chinese Academy of Sciences，Beijing 100080，China，Institute of Chemistry，Chinese Academy of Sciences，Beijing 100080，China，Institute of Chemistry，Chinese Academy of Sciences，Beijing 100080，China |
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| 基金项目： | Project (Nos. 29602010, 29772037) supported by the National Natural Science Foundation of China. |
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| 摘 要： | Calix4] (aza) crowns containing amide groups 3a-d were synthesized by the reactions of calix4]arene (1a) or p-tert-butylcalix4]arene (1b) with N, N'-ethylenebis(2-chloroac-etamide) (2a) or N, N'-1,2-phenylenebis(2-chloroacetamide) (2b) by one step procedure in yields of 85-90% . Calix4]-(aza) crowns 4a-b could be obtained by the reduction of 3a-b with LiAlH4 in yields of 51 and 67% , respectively. The nitration of 3a or 3c afforded new chromogenic calix4]arenes 5a bearing two nitrophenol moieties and 5c bearing one nitro-phenol and one quinone moiety, respectively. The ipso-nitrations of 3b and 3d were also studied. Both gave the products containing one nitrophenol and one quinone moiety. Moreover, a very interesting calix4]arene derivative 5d containing one cyclohexadienone moiety was also separated as the main product when 3d was ipso -nitrated.
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Synthesis and nitration of calix[4] (aza)crowns |
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| ZHENG,Qi-Yu CHEN,Chuan-Feng HUANG,Zhi-TangInstitute of Chemistry,Chinese Academy of Sciences,Beijing ,China.Synthesis and nitration of calix[4] (aza)crowns[J].Chinese Journal of Chemistry,2000,18(1):104-111. |
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| Authors: | ZHENG Qi-Yu CHEN Chuan-Feng HUANG Zhi-TangInstitute of Chemistry Chinese Academy of Sciences Beijing China |
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| Institution: | ZHENG,Qi-Yu CHEN,Chuan-Feng HUANG,Zhi-TangInstitute of Chemistry,Chinese Academy of Sciences,Beijing 100080,China |
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| Abstract: | Calix4] (aza) crowns containing amide groups 3a-d were synthesized by the reactions of calix4]arene (1a) or p-tert-butylcalix4]arene (1b) with N, N'-ethylenebis(2-chloroac-etamide) (2a) or N, N'-1,2-phenylenebis(2-chloroacetamide) (2b) by one step procedure in yields of 85-90% . Calix4]-(aza) crowns 4a-b could be obtained by the reduction of 3a-b with LiAlH4 in yields of 51 and 67% , respectively. The nitration of 3a or 3c afforded new chromogenic calix4]arenes 5a bearing two nitrophenol moieties and 5c bearing one nitro-phenol and one quinone moiety, respectively. The ipso-nitrations of 3b and 3d were also studied. Both gave the products containing one nitrophenol and one quinone moiety. Moreover, a very interesting calix4]arene derivative 5d containing one cyclohexadienone moiety was also separated as the main product when 3d was ipso -nitrated. |
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| Keywords: | Calix[4] (aza) crown calixarene nitration reduction |
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