English
新闻公告
More
化学进展 1997, Vol. 9 Issue (03): 300- 前一篇   后一篇

• 综述与评论 •

C60的加成反应

唐光诗;朱鹤孙;董树安   

  1. (北京理工大学材料科学研究中心 北京 100081; 山东师范大学有机化学所 济南 250014)
  • 收稿日期:1996-08-01 修回日期:1997-05-01 出版日期:1997-09-24 发布日期:1997-09-24

The Addition Reaction of C60

Tang Guang shi;Zhu Hesun;Dong Shuan   

  1. (Research Center of Materials Science,Beijing Institute of Technology, Beijing 100081, China; Institute of Organic Chemistry, Shandong Normal University, J inan 250014, China)
  • Received:1996-08-01 Revised:1997-05-01 Online:1997-09-24 Published:1997-09-24

富勒烯化学是以全碳分子球烯为母体的新兴有机化学领域, 在材料、医学及立体化学合成方法等方面具有广泛的应用和发展前景。本文综述了C60的加成反应, 较全面地展示了富勒烯的化学性质。

关键词: C60, 加成反应

Fullerene chemistry is a new research field concerning compounds with all carbon spherical molecules as their parents. It has potential applications in materials science, medical science and synthesis methods of sterochemistry. This review summarized the addition reaction of C60 and revealed the chemical properties of fullerene.

中图分类号: 

()

[1 ] Kroto H W , Heath J H, O ‘Brien S C, Curl R F, Smalley R E, Nature, 1985, 318, 162.
[2 ] Kratscher W , Lamb L D, Fostiropoulos K, Hufman D R, Nature, 1990, 347, 354.
[3 ] Hirsch A , The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994.
[4 ] Matsuzawa N , Dixon D A , Fukunaga T , J. Phys. Chem. , 1992, 96, 7594.
[5 ] Hirsch A , Grosser T , Skiebe A , SoiA , Chem. Ber. , 1993, 126, 1061.
[6 ] Hirsch A , Lamparth I, Karfunkel H R, Angew. Chem. Int. Ed. Engl. , 1994, 33, 437.
[7 ] Bestmann H J , Hadawi D, Roder T , Moll C, Tetrahedron Lett. , 1994, 9017.
[8 ] Yamago S, Yanagawa M , Nakamura E, J. Chem. Soc. , Chem. Commun. , 1994, 2093.
[9 ] Hirsch A , Li Q , Wuld F, Angew. Chem. Int. Ed. Engl. , 1991, 30, 1309.
[10 ] Schick G, Kampe K D, Hirsch A. J. Chem. Soc. , Chem. Commun. , 1995, 2032.
[11 ] Kampe K D, Egger N , Vogel M , Angew. Chem. Int. Ed. Engl. , 1993, 32, 1174.
[12 ] Gan L , Zhou D, Luo C, Tan H, Huang C, Lu M , Pan J , Wu Y, J. Org. Chem. , 1996, 61, 1954.
[13 ] Liou K, Cheng C, J. Chem. Soc. , Chem. Commun. , 1996, 1423.
[14 ] Tsuda M , Ishda T , Nogami T , Kurono S, Ohashi M , J. Chem. Soc. , Chem. Commun. , 1993,1296.
[15 ] Prato M , Suzuki T , Foroudian H, Li Q , Khemani K, Wudl F, J. Am. Chem. Soc. , 1993, 115,1594.
[16 ] Krautler B, Puchberger M , Helv. Chim. Acta, 1993, 76, 1626.
[17 ] Rubin Y, Khan S, Freedberg D I, Yeretzian C, J. Am. Chem. Soc. , 1993, 115, 344.
[18 ] An Y Z, Anderson J L , Rubin Y, J. Org. Chem. , 1993, 58, 4799.
[19 ] Lissen T G, Durr K, Hirsch A , Hanack M , J. Chem. Soc. , Chem. Commun. , 1995, 103.
[20 ] Khan S I, Oliver A M , Paddon M N , Rubin Y, J. Am. Chem. Soc. , 1993, 115, 4919.
[21 ] Belik P, GugelA , Spikermann J , Mullen K, Angew. Chem. Int. Ed. Engl. , 1993, 32, 78.
[22 ] Diederich F, Jonas U , Gramlich V , Hermann A , Ringsdof H, Thilgen C, Helv. Chim. Acta, 1993,76, 2445.
[23 ] Bidell W , Douthwaite R E, Green M L , Stephens H, Turner C, J. Chem. Soc. , Chem. Commun. ,1994, 1641.
[24 ] Gugel A , Kras A , Spikermann J , Belik P, Mullen K, Angew. Chem. Int. Ed. Engl. , 1994, 33,559.
[25 ] Iyoda M , Sultana F, Sasaki S, Yoshida M , J. Chem. Soc. , Chem. Commun. , 1994, 1929 .
[26 ] Zhang X, Foote C S, J. Org. Chem. , 1994, 59, 5235.
[27 ] Suzuki T , Li Q , Khemani K C, Wuld F, Almarsson O , Science, 1991, 254, 1186.
[28 ] Suzuki T , Li Q , Khemani K C, Wuld F, J. Am. Chem. Soc. , 1992, 114, 7301.
[29 ] Shi S, Khemani K C, Li Q , Wuld F, J. Am. Chem. Soc. , 1992, 114, 10656.
[30 ] Skiebe A , Hirsch A , J. Chem. Soc. , Chem. Commun. , 1994, 335.
[31 ] Issacs L , Wehrig A , Diederich F, Helv. Chim. Acta, 1993, 76, 1231.
[32 ] Diederich F, Issacs L , Philp D, Chem. Soc. Rev. , 1994, 243.
[33 ] Prato M , LiQ , Wuld F, LucchiniV , J. Am. Chem. Soc. , 1993, 115, 1148.
[34 ] Grosser T , Prato M , LucchiniV , Hirsch A , Wuld F, Angew. Chem. Int. Ed. Engl. , 1995, 34,1343 .
[35 ] Yamago S, Nakamura M , Nakamura E, Prato M , Wuld F, J. Org. Chem. , 1993, 58, 4796.
[36 ] Hoke S H, Molstad J , Yang S S, Carlson D, Kahr B, J. Org. Chem. , 1994, 59, 3230.
[37 ] Maggini M , Scorrano G, Prato, M , J. Am. Chem. Soc. , 1993, 115, 9798.
[38 ] Maggini M , Scorrano G, Bianco A , Toniolo C, Sijbesma P, Wudl F, Prato M , J. Chem. Soc. ,Chem. Commun. , 1994, 305.
[39 ] Meier M S, Poplamsska M , J. Org. Chem. , 1993, 58, 4524.
[40 ] Gonzalez R, Knight B W , Wudl F, SemonesM A , Padwa A , J. Org. Chem. , 1994, 59, 7949.
[41 ] Arbogast J W , Foote C S, Kao M , J. Am. Chem. Soc. , 1992, 114, 2277.
[42 ] Akaska T , Ando W , Kobayashi K, Nagasa S, J. Am. Chem. Soc. , 1993, 115, 10366.
[43 ] Hoke II S H, Molstad J , Dilattato D, Jay M J , Carlson D, Karl B, Cooks R G, J. Org. Chem. ,1992, 57, 5069.
[44 ] Prato M , Maggini M , Scorrano G, LucchiniV , J. Am. Chem. Soc. , 1993, 58, 3613.
[45 ] Zhang X, Romero A , Foote C S, J. Am. Chem. Soc. , 1993, 115, 11024.
[46 ] Wilson S R, Wu Y, Kaprinidis N A , Schuster D I, J. Am. Chem. Soc. , 1993, 115, 8495.
[47 ] Wilson S R, Wu Y, Kaprinidis N A , Schuster D I, J. Org. Chem. , 1993, 58, 6548.
[48 ] An Y Z, Rubin Y, Schaller C, McElvany S W , J. Org. Chem. , 1994, 59, 2927.
[49 ] Anderson H L , Faust R, Rubin Y, Diederich F, Angew. Chem. Int. Ed. Engl. , 1994, 33, 1366.
[50 ] Tsuda M , Ishida T , Nogami T , Curono S, Ohashi M , Tetrahedron Lett. , 1993, 34, 6911.
[51 ] Merlic C A , Bendorf H D, Tetrahedron Lett. , 1994, 35, 9529.
[52 ] Akaska T , Ando W , Kobayashi K, Nagasa S, J. Am. Chem. Soc. , 1993, 115, 1605.
[53 ] Banks M R, Cadogan J I G, Gosney I, Hodgson G, Langridge R, Millar A , J. Chem. Soc. , Chem.Commun. , 1994, 1355.
[54 ] Banks M R, Cadogan G, Gosney I, Hodgson G, Langridge S R, Millar A , Tetrahedron Lett. , 1994,35, 9067.
[55 ] Beer E, Feuerer M , Knorr A , Mirlach A , Dsub J , Angew. Chem. Int. Ed. Engl. , 1994, 33,1087.
[56 ] Ballenweg S, Gleiter R, Kratschmer W , J. Chem. Soc. , Chem. Commun. , 1994, 2269.
[57 ] Haufler R E, Conceicao J , Chibante L P F, Chai Y, J. Phys. Chem. , 1990, 94, 8634.
[58 ] Banks M R, Dale M J , Gonsny I, Hodgson K G, J. Chem. Soc. , Chem. Commun. , 1993, 1149.
[59 ] Ruchhardt C, Gerst M , Ebenhoch J , Bechous H D, Angew. Chem. Int. Ed. Engl. , 1993, 32, 584.
[60 ] Attala M I, Vassallo A M , Tattam B N , Hanna J V , J. Phys. Chem. , 1993, 97, 6329.
[61 ] Henderson C C, Cahill P A , Science, 1993, 259, 1885.
[62 ] Guarr T F, Meier M S, Vance V K, Clayton M , J. Am. Chem. Soc. , 1993, 115, 9862.
[63 ] Henderson C C, Assink R A , Cahill P A , Angew. Chem. Int. Ed. Engl. , 1994, 33, 786.
[64 ] Fagan P J , Calabrese J C, Malone B, Acc. Chem. Res. , 1992, 25, 134.
[65 ] Balch A L , Lee J M , Noll B C, Omstead M M , J. Am. Chem. Soc. , 1992, 114, 10984.
[66 ] Balch A L , Lee J M , Noll B C, Omstead M M , Inorg. Chem. , 1993, 32, 3577.
[67 ] Bellenweg S, Geileiter R, Kratschmer W , Tetrahedron Lett. , 1993, 34, 3737.
[68 ] Thorp H H, Karlsbeck W A , J. Electroanal. Chem. , 1991, 314, 363.
[69 ] Creegan K M , Robbins J L , Robbins W K, Millar J M , Sherwood R D, Tindall P G, Cox D M ,Smith B, McCauly P, Jones D R, Gallagher R T , J. Am. Chem. Soc. , 1992, 114, 1103.
[70 ] Elemes Y, Silverman S K, Sheu C, Kao M , Foote C S, Alvarez M M , Whetten R L , Angew.Chem. Int. Ed. Engl. , 1992, 31, 351.
[71 ] Hawkins J M , Meyer A , Lewis T A , Loren S D, Hollander F J , Science, 1991, 252, 312.
[72 ] Hawkins J M , Meyer A , Nanbu M , J. Am. Chem. Soc. , 1993, 115, 9844.
[73 ] Holloway J H, Hope E G, Taylor R, Lanley G L , Advent A G, Denis T J , Hare J H, Kroto H W ,Walton M , J. Chem. Soc. , Chem. Commun. , 1991, 966.
[74 ] Kniaz K, Fischer J E, Selig H, Vaughan M , Romanov W J , Cox D M , Chowdhury K, McCauley J P, J. Am. Chem. Soc. , 1993, 115, 6060.
[75 ] Gakh A A , Tuinman A A , Adcock J L , Sachleben R A , Compton R N , J. Am. Chem. Soc. , 1994,116, 819.
[76 ] Tuinman A A , Gakh A A , Adcock J L , Compton R N , J. Am. Chem. Soc. , 1993, 115, 5885.
[77 ] Olah G A , Bucsi I, Lambert C, Aniszfeld R, TrivediN J , Prakash S, J. Am. Chem. Soc. , 1991,113, 9385.
[78 ] Tebbe F N , Becker J Y, ChaseD B, Firment L E, Holler E R, Malome B S, Krusic P J , Wasserman E, J. Am. Chem. Soc. , 1991, 113, 9900.
[79 ] Birkett P R, Avent A G, Darwish A D, Kroto H W , Taylor R, Walton M , J. Chem. Soc. , Chem.Commun. , 1993, 1230.
[80 ] Tebbe F N , Harlow R L , Chase D B, Thorn D L , Campbell J C, Calabress J C, Herron N , Youn R G, Wasserman E, Science, 1992, 256, 822.
[81 ] Birkett P R, Hitchcock P B, Kroto H W , Taylor R, Walton M , Nature, 1992, 357, 479.
[82 ] Miller G P, Mat. Res. Soc. Symp. Proc. , 1992, 247, 293.
[83 ] Thoman H, Bernardo M , Miller G P, J. Am. Chem. Soc. , 1992, 114, 6593.
[84 ] Chiang L Y, Swirczewski J W , Hsu C S, Chowdhury S K, Cameron S, Cressgan K, J. Chem. Soc. ,Chem. Commun. , 1992, 1791.
[85 ] Chiang L Y, Upasani R B, Swirczewski J W , Soled S, J. Am. Chem. Soc. , 1993, 115, 5354.
[86 ] Hirsh A , Lamparth I, Grosser T , Karfunkel H R, J. Am. Chem. Soc. , 1994, 116, 9385.
[87 ] Isaacs L , Haldimann R F, Diederich F, Angew. Chem. Int. Ed. Engl. , 1994, 34, 2434.
[88 ] Krautler B, Maynollo J , Angew. Chem. Int. Ed. Engl. , 1994, 34, 87.
[89 ] Nalwa H S, Advan. Mater. , 1993, 5, 341.
[90 ] Friedman S M , DeCamp D P, Sijbesma R P, J. Am. Chem. Soc. , 1993, 115, 6506.
[91 ] Tokuyama H, Yamago S, Nakamura E, J. Am. Chem. Soc. , 1993, 115, 7918.

[1] 曹如月, 肖晶晶, 王伊轩, 李翔宇, 冯岸超, 张立群. 杂Diels-Alder 环加成反应级联RAFT聚合[J]. 化学进展, 2023, 35(5): 721-734.
[2] 董军, 许家喜. 烯亚砜化合物的制备及反应概述[J]. 化学进展, 2022, 34(5): 1088-1108.
[3] 廖伊铭, 吴宝琪, 唐荣志, 林峰, 谭余. 环张力促进的叠氮-炔环加成反应[J]. 化学进展, 2022, 34(10): 2134-2145.
[4] 章强, 黄文峻, 王延斌, 李兴建, 张宜恒. 基于铜催化叠氮-炔环加成反应的聚氨酯功能化[J]. 化学进展, 2020, 32(2/3): 147-161.
[5] 李路瑶, 徐鑫尧, 朱博, 常俊标. 吡唑酮化合物在催化不对称反应中的应用[J]. 化学进展, 2020, 32(11): 1710-1728.
[6] 王灯旭, 曹金风, 韩栋栋, 李文思, 冯圣玉. 有机硅合成新方法[J]. 化学进展, 2019, 31(1): 110-120.
[7] 方德彩*. [2+2]环加成反应机理的理论研究[J]. 化学进展, 2012, 24(06): 879-885.
[8] 杨绳岩, 吴振奕, 万新军, 晏娟. 卟啉-富勒烯络合物的合成[J]. 化学进展, 2011, 23(6): 1123-1136.
[9] 王春,刘伟华,周欣,李越敏,李云鹏. 有机催化不对称[4+2]环加成反应*[J]. 化学进展, 2009, 21(09): 1857-1868.
[10] 张韶光,刘俊辉,张文雄,席振峰. 硅杂六元环化合物的反应* [J]. 化学进展, 2009, 21(0708): 1487-1493.
[11] 方钊,唐瑞仁,罗佐文. 烯酮中间体及其在不对称环加成反应中的应用[J]. 化学进展, 2008, 20(10): 1544-1552.
[12] 张璞,吕爽,郭志新. 双亲性C60衍生物水相聚集行为*[J]. 化学进展, 2008, 20(04): 548-557.
[13] 高爽,胡信全,郑卓. 轴向手性膦氮配体及其在不对称催化合成中的应用[J]. 化学进展, 2002, 14(06): 438-.
[14] 许家喜,焦鹏. 固相载体上的环加成反应及其应用[J]. 化学进展, 2000, 12(02): 131-.
[15] 郭可信. 二十面体壳层结构——纪念C60发现10周年[J]. 化学进展, 1995, 7(04): 253-.
阅读次数
全文


摘要

C60的加成反应