中文 |
English |
Email Alert
α-羰基重氮化合物的卡宾聚合反应研究
Carbene Polymerization of α-Carbonyl Diazo Compounds
α-羰基重氮化合物的卡宾聚合反应（C1聚合反应）是近年发展起来的一类合成碳链聚合物的新反应类型， 为合成碳链上每一个碳原子都连接有极性取代基的高度功能化聚烯烃类似物提供了烯烃聚合（C2聚合）无法替代且更为便捷有效的新途径，在功能高分子领域有广阔应用前景。本文详细描述了重氮乙酸酯、重氮乙酰胺和α-重氮酮等化合物在铜、钯、铑等过渡金属催化下的卡宾聚合反应及其反应机理，论述了α-重氮化合物参与的共聚合反应以及双-α-羰基重氮化合物的卡宾聚合反应和共聚合反应。最后，展望了卡宾聚合反应的发展趋势。
Carbene polymerization of α-diazocarbonyl compounds is a new type reaction which has been developed in recent years for the synthesis of functional polymers with an ester group at every backbone carbon atom. Carbene polymerization which differs from traditional and classic vinyl polymerizations offers a convenient and useful method to obtain polyolefins, leading to a wide range of applications in various fields. This review describes the carbene polymerization of diazo compounds (diazoacetate, diazoacetamide, α-diazoketone) in the presence of transition metals (such as copper, palladium and rhodium) and the relevant mechanisms. Besides, the copolymerizations of α-diazo compound with each other, as well as other kinds of reagents, are indicated in detail. Moreover, the carbene (co)polymerization of bisdiazo compounds are introduced. Finally, the future outlook of carbene polymerization is suggested.
Contents
1 Introduction
2 Carbene polymerizations of diazo compounds
2.1 Palladium-mediated carbene polymerizations of diazo compounds
2.2 Rhodium-mediated polymerizations of diazo compounds
2.3 Copolymerizations of diazo compounds
2.4 Carbene polymerizations of bisdiazo compounds
3 Copolymerizations of carbene polymerization with other kinds of monomers
3.1 Copolymerization of carbene with alkene
3.2 Copolymerization of carbene with alkyne
3.3 Copolymerization of carbene polymerization with cyclic monomer
4 Conclusion and outlook
carbene polymerization
[1] Jellema E, Jongerius A L, Reek J N, Bruin B. Chem. Soc. Rev., 2010, 39:1706.
[2] 赵健 (Zhao J), 吕英萤 (Lv Y Y), 胡友良 (Hu Y L). 化学进展 (Progress in Chemistry), 2001, 13(1):48.
[3] 李启蒸 (Li Q Z), 张国艺 (Zhang G Y), 袁聪 (Yuan C), 魏柳荷 (Wei L H), 马志 (Ma Z). 化学进展 (Progress in Chemistry), 2011, 23(6):1174.
[4] 赵艳 (Zhao Y), 郭彩红 (Guo C H), 武海顺 (Wu H S). 化学进展 (Progress in Chemistry), 2014, 26(2/3):345.
[5] Moscato B M, Zhu B, Landis C R. J. Am. Chem. Soc., 2010, 132:14352.
[6] Xiao L Q, Li Y, Liao L Q, Liu L J. New J. Chem., 2013, 37:1874.
[7] Kim H, Kobayashi S, AbdurRahim M A, Zhang M J, Khusainova A, Hillmyer M A, Abdala A A, Macosko C W. Polymer, 2011, 52:1837.
[8] Song P, Cao Z, Cai Y, Zhao L, Fang Z, Fu S. Polymer, 2011, 52:4001.
[9] Baba E, Honda S, Yamamoto T, Tezuka Y. Polym. Chem., 2012, 3:1903.
[10] Marques M M, Correia S G, Ascenso J R, Ribeiro A F G, Gomes P T, Dias A R, Foster P, Rausch M D, Chien J C W. J. Polym. Sci., Part A: Polym. Chem., 1999, 37:2457.
[11] Peng C H, Zhong M, Wang Y, Kwak Y, Zhang Y, Zhu W, Tonge M, Buback J, Park S, Krys P. Macromolecules, 2013, 46:3803.
[12] Wang Y, Schroeder H, Morick J, Buback M, Matyjaszewski K. Macromol. Rapid Commun., 2013, 34:604.
[13] 刘长坤 (Liu C K), 金国新 (Jin G X). 化学学报 (Acta Chimica Sinica), 2002, 60(1):157.
[14] Boffa L S, Novak B M. Chem. Rev., 2000, 100:1479.
[15] Ran J, Wu L, Zhang Z, Xu T. Prog. Polym. Sci., 2014, 39:124.
[16] Fernandes N J, Koerner H, Giannelis E P, Vaia R A. MRS Commun., 2013, 3:13.
[17] Takeuchi D. MRS Bull., 2013, 38:252.
[18] Wei J, Hwang W, Zhang W, Sita L R. J. Am. Chem. Soc., 2013, 135:2132.
[19] Hu Y, Wang X, Chen Y, Caporaso L, Cavallo L, Chen E Y X. Organometallics, 2013, 32:1459.
[20] Brintzinger H H, Fischer D, Mülhaupt R, Rieger B, Waymouth R M. Angew. Chem. Int. Ed., 1995, 34:1143.
[21] Naoyuki T M Y, Takayuki O. Polym. J., 1983, 15:255.
[22] Pechmann H. Ber. Deutsch. Chem. Ges., 1898, 31:2640.
[23] Bamberger E, Tschirner F. Ber. Deutsch. Chem. Ges., 1900, 33:955.
[24] Doyle M P, Duffy R, Ratnikov M, Zhou L. Chem. Rev., 2010, 110: 704.
[25] Liu L, Song Y, Li H. Polym. Int., 2002, 51:1047.
[26] Ihara E, Haida N, Iio M, Inoue K. Macromolecules, 2003, 36:36.
[27] Ihara E, Fujioka M, Haida N, Itoh T, Inoue K. Macromolecules, 2005, 38: 2101.
[28] Ihara E. Adv. Polym. Sci., 2010, 231:191.
[29] Ihara E, Ishiguro Y, Yoshida N, Hiraren T, Itoh T, Inoue K. Macromolecules, 2009, 42:8608.
[30] Ihara E, Hiraren T, Itoh T, Inoue K. Polym. J., 2008, 40:1094.
[31] Ihara E, Hiraren T, Itoh T, Inoue K. J. Polym. Sci., Part A: Polym. Chem., 2008, 46:1638.
[32] Ihara E, Kida M, Fujioka M, Haida N, Itoh T, Inoue K. J. Polym. Sci., Part A: Polym. Chem., 2007, 45:1536.
[33] Franssen N M, Reek J N, Bruin B. Chem. Soc. Rev., 2013, 42:5809.
[34] Ihara E, Nakada A, Itoh T, Inoue K. Macromolecules, 2006, 39:6440.
[35] Ihara E, Okada R, Sogai T, Asano T, Kida M, Inoue K, Itoh T, Shimomoto H, Ishibashi Y, Asahi T. J. Polym. Sci., Part A: Polym. Chem., 2013, 51:1020.
[36] Ihara E, Goto Y, Itoh T, Inoue K. Polym. J., 2009, 41:1117.
[37] Hetterscheid D G H, Hendriksen C, Dzik W I, Smits J M M, Eck E R H, Rowan A E, Busico V, Vacatello M, Castelli V V, Segre A, Jellema E, Bloemberg T G, Bruin B. J. Am. Chem. Soc., 2006, 128:9746.
[38] Noels A F. Angew. Chem. Int. Ed., 2007, 46:1208.
[39] Jellema E, Jongerius A L, Walters A J C, Smits J M M, Reek J N H, Bruin B. Organometallics, 2010, 29:2823.
[40] Jellema E, Jongerius A L, Ekenstein G A, Mookhoek S D, Dingemans T J, Reingruber E M, Chojnacka A, Schoenmakers P J, Sprenkels R, Eck E R H, Reek J N H, Bruin B. Macromolecules, 2010, 43:8892.
[41] Franssen N M, Reek J N, Bruin B. Dalton Trans., 2013, 42:9058.
[42] Franssen N M, Finger M, Reek J N, Bruin B. Dalton Trans., 2013, 42:4139.
[43] Walters A J C, Troeppner O, Ivanovic-Burmazovic I, Tejel C, Rio M P, Reek J N H, Bruin B. Angew. Chem. Int. Ed., 2012, 51:5157.
[44] Walters A J C, Jellema E, Finger M, Aarnoutse P, Smits J M M, Reek J N H, Bruin B. ACS Catal., 2012, 2:246.
[45] Suarez A I O, Río M P, Remerie K, Reek J N H, Bruin B. ACS Catal., 2012, 2:2046.
[46] Franssen N M G, Rernerie K, Macko T, Reek J N H, Bruin B. Macromolecules, 2012, 45:3711.
[47] Franssen N M G, Walters A J C, Reek J N H, Bruin B. Cat. Sci. Techn., 2011, 1:153.
[48] Ihara E, Nishida H, Fujii M, Itoh T, Inoue K. Polym. Bull., 2011, 66:3.
[49] Franssen N M G, Reek J N H, Bruin B. Polym. Chem., 2011, 2:422.
[50] Xiao L, Liao L, Guo X, Liu L. Macromol. Chem. Phys., 2013, 214:2500.
[51] Xiao L, Li Y, Jia X, Liao L, Liu L. Polym. Int., 2014, 63(7): 1154.
/
| 〈 |
|
〉 |
PDF
(2261KB)
