葫芦脲的分解氧化研究
收稿日期: 2014-09-03
修回日期: 2014-10-27
网络出版日期: 2014-11-05
基金资助
北京理工大学基础研究基金(No. 20131042006)资助项目.
Oxidation of Cucurbituril and Its Analogues
Received date: 2014-09-03
Revised date: 2014-10-27
Online published: 2014-11-05
Supported by
Project supported by the Basic Research Fund of Beijing Institute of Technology (No. 20131042006).
路红燕 , 史大昕 , 张奇 , 杨德利 , 李加荣 . 葫芦脲的分解氧化研究[J]. 有机化学, 2015 , 35(2) : 467 -471 . DOI: 10.6023/cjoc201409002
Cucurbituril is a high symmetry and rigid structure. When cucurbit[6]uril (CB[6]) was oxidized with persulfate (e.g. potassium persulfate, sodium persulfate and ammonium persulfate), the main product was perhydroxy-cucurbituril and the minor one was oxalic acid. Oxalic acid was also obtained by the oxidization of both CB[n] (n=5, 7, 8) and perhydrox-cucurbituril with various persulfates. As far as we know, this is the first time to discover that both cucurbit[n]uril and perhydrox-cucurbit[n]uril can be destroyed to give a small molecule-oxalic acid.
Key words： cucurbituril; perhydroxy-cucurbituril; oxidation; oxalic acid
[1] Behrend, R.; Meyer, E.; Rusche, F. Liebigs Ann. Chem. 1905, 339, 1.
[2] Freeman, W. A.; Mock, W. L.; Shih, N. Y. J. Am. Chem. Soc. 1981, 103, 7367.
[3] Kim, J.; Jung, I. S.; Kim, S. Y.; Lee, E.; Kang, J. K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540.
[4] Day, A. I.; Arnold, A. P.; Blanch, R. J.; Snushall, B. J. Org. Chem. 2001, 66, 8094.
[5] Day, A. I.; Blanch, R. J.; Arnold, A. P.; Lorenzo, S.; Lewis, G. R.; Dance, I. Angew. Chem. Int. Ed. 2002, 41, 275.
[6] Liu, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 16798.
[7] Cheng, X. J.; Liang, L. L.; Chen, K.; Ji, N. N.; Xiao, X.; Zhang, J. X.; Zhang, Y. Q.; Xue, S. F.; Zhu, Q. J.; Ni, X. L.; Tao, Z. Angew. Chem. Int. Ed. 2013, 52, 7252.
[8] Isaacs, L.; Park, S. K.; Liu, S.; Ko, Y. H.; Selvapalam, N.; Kim, Y.; Kim, H.; Zavalij, P. Y.; Kim, G. H.; Lee, H. S.; Kim, K. J. Am. Chem. Soc. 2005, 127, 18000.
[9] Han, C. Y.; Zhang, Z. B.; Chi, X. D.; Zhang, M. M.; Yu, G. C.; Huang, F. H. Acta Chim. Sinica 2012, 70, 1775 (in Chinese). (韩成友, 张子彬, 池小东, 张明明, 喻国灿, 黄飞鹤, 化学学报, 2012, 70, 1775.)
[10] Zheng, R.; Liang, D. X.; Yu, X. T.; Chen, R. E.; Jiang, H. J.; Zhou, Q. Z. Chin. J. Org. Chem. 2013, 33, 504 (in Chinese). (郑睿, 梁丹霞, 于雪涛, 陈仁尔, 蒋华江, 周其忠, 有机化学, 2013, 33, 504.)
[11] Ma, M. F.; Xing, P. Y.; Li, S. Y.; Chu, X. X.; Wang, B.; Hao, A. Y. Prog. Chem. 2014, (8), 1317 (in Chinese). (马明放, 邢鹏遥, 李尚洋, 初晓晓, 王波, 郝爱友, 化学进展, 2014, (8), 1317.)
[12] (a) Boissonnas, R. A.; Blodinger, J.; Welcher, A. D. J. Am. Chem. Soc. 1952, 74, 5309.
(b) Anna, B.; Gerald, P.; Dendroamide, A. Heterocycle 2002, 58, 521.
[13] Han, B. H.; Liu, Y. Chin. J. Org. Chem. 2003, 23, 139 (in Chinese). (韩宝航, 刘育, 有机化学, 2003, 23, 139.)
[14] Lee, W.; Samal, S.; Selvapalam, N.; Kim, H. J.; Kim, K. Acc. Chem. Res. 2003, 36, 621.
[15] (a) Flinn, A.; Hough, G. C.; Stoddart, J. F.; Williams, D. J. Angew. Chem. Int. Ed. 1992, 31, 1475.
(b) Zhao, J.; Kim, H. J.; Oh, J.; Kim, S. Y.; Lee, J. W.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 4233.
(c) Isobe, H.; Sato, S.; Nakamura, E. Org. Lett. 2002, 4, 1287.
(d) Miyahara, Y.; Abe, K.; Inazu, T. Angew. Chem., Int. Ed. 2002, 41, 3020.
(e) Day, A. I.; Arnold, A. P.; Blanch, R. J. Molecules 2003, 8, 74.
(f) Vinciguerra, B.; Cao, L.; Cannon, J. R.; Zavalij, P. Y.; Fenselau, C.; Isaacs, L. J. Am. Chem. Soc. 2012, 134, 13133.
[16] Lucas, D.; Minami, T.; Iannuzzi, G.; Cao, L.; Wittenberg, J. B.; Jr, P. A.; Isaacs, L. J. Am. Chem. Soc. 2011, 133, 17966.
[17] Cao, L.; Isaacs, L. Org. Lett. 2012, 14, 3072.
[18] Gilberg, L.; Khan, M. S. A.; Enderesova, M.; Sindelar, V. Org. Lett. 2014, 16, 2446.
[19] Jon, S. Y.; Selvapalam, N.; Oh, D. H.; Kang, J. K.; Kim, S. Y.; Kim, K. J. Am. Chem. Soc. 2003, 125, 10186.
[20] Zhao, N.; Lloyd, G. O.; Scherman, O. A. Chem. Commun. 2012, 48, 3070.
[21] Meng, F. M.S. Thesis, Guizhou University, Guizhou, 2006 (in Chinese). (孟飞, 硕士论文, 贵州大学, 贵州, 2006.)
[22] Bi, Q.; Hu, Y. P.; Yang, Q.; Ma, C. L.; Li, D. L. Chin. J. Org. Chem. 2007, 27, 880 (in Chinese). (毕强, 胡英鹏, 杨琴, 马彩莲, 李东亮, 有机化学, 2007, 27, 880.)
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