吡啶鎓盐系列等相转移催化剂的合成、固载化及催化活性研究
摘要
相转移催化技术(phase-transfer catalysis)是在20世纪70年代初发展起来的有机合成新技术，己被广泛地应用于聚合物、医药、农药、精细化学品等的合成。相转移催化具有许多优点，如反应条件温和，可提高反应速率和产率等。相转移催化剂固载化可以解决产物分离困难、催化剂重复使用等问题，是当前研究的热点之一。本论文对传统相转移催化氟化和固一固一液三相相转移催化酯化反应进行了系统的研究。
第一部分研究内容：
含氟芳香族化合物是农药、医药等的重要中间体，其特殊的应用价值和潜在的经济价值，引起了许多研究工作者和化工生产厂家的注意。通过卤离子交换法制备含氟芳香族化合物是目前颇受重视的方法，但反应需在较高的温度下进行。由于4-二烷基氨基吡啶中供电子的二烷基与吡啶环共振，使正电荷分散于多个原子中，稳定性比吡啶增加。论文系统研究了具有高热稳定性和催化活性的吡啶翁盐系列新型相转移催化剂。
成功地合成了4-二甲氨基吡啶环中N-烷基分别为正丁基、(2-乙基)己基、三苯甲基、苄基、正十二烷基的吡啶翁盐系列相转移催化剂。通过~1HNMR、mp、IR、MS对催化剂进行了结构鉴定。差热分析表明该系列催化剂具有较好的耐高温性能。
研究了该系列催化剂在芳香氯化物与KF的卤离子交换氟化反应中的催化活性，表明其具有良好的反应活性和热稳定性。通过系统地考察KF的用量、催化剂中N-烷基的结构、催化剂中阴离子的结构、反应溶剂、反应温度、芳香氯化物的不同取代基等对催化剂活性的影响等，筛选出催化活性最好的催化剂为4-二甲氨基-N-(2-乙基)己基吡啶鎓盐。在该催化剂作用下，只需反应1.5小时，对氯硝基苯氟化为对氟硝基苯的得率即可高达98.6％。
第二部分研究内容：
乙酸苄酯是一种重要的香精配料，具有新鲜果香的茉莉型香气，应用非常广
Catalysis is a useful technology in organic synthesis. Phase-transfer catalyst (PTC) has the considerable advantages, such as permitting reaction carry out under moderate condition, improving reaction rates and yields. In order to dissolve shortcomings existing in homogeneous, immobilization of PTC is one of the current interest to chemist. In this dissertation, traditional phase-transfer fluorination and solid-solid-liquid triphase-transfer esterification were studied, respectively.
The first section:
Fluorine-containing aromatic compounds are of current interest because of their special chemical and biological properties in agricultural and pharmaceutical research areas. Although a number of methods for the introducing fluorine into the organic molecules have been developed and successfully utilized for synthesis of fluoro aromatic compounds, halogen-exchange by potassium fluoride (KF) seems to be one of the most practical and useful methods. This kind of reaction must be carried out under elevated temperature.
4-(N', N'-dialkylamino) pyridinium salts are the new phase-transfer catalysts. They have higher thermal stabilities than normal pyridinum salts because of the resonance of dialkylamino and pyridine ring, which make the positive charge delocalized in multiple atoms. In this paper, a series of thermal stable PTC based on dimethylamino pyridinium salts were synthesized and characterized by ~1HNMR, mp, IR, and MS. The activities of the catalysts were evaluated in the typical aromatic nucleophilic substitution reaction (fluorination) and the excellent results were obtained.
The effects of various reaction conditions such as molar ratio of KF, structure of N-alkyl and anions, the type of substituents in substrates, reaction solvent, and temperature on the activities of catalysts were investigated in detail. Among the catalysts prepared, 4-(N', N'-dimethylamino)-N-ethylhexyl pyridinium salt (Cat2) exhibited the highest catalytic activity. It gave p-nitrofluorobenzene in yield up to
第一部分研究内容：
含氟芳香族化合物是农药、医药等的重要中间体，其特殊的应用价值和潜在的经济价值，引起了许多研究工作者和化工生产厂家的注意。通过卤离子交换法制备含氟芳香族化合物是目前颇受重视的方法，但反应需在较高的温度下进行。由于4-二烷基氨基吡啶中供电子的二烷基与吡啶环共振，使正电荷分散于多个原子中，稳定性比吡啶增加。论文系统研究了具有高热稳定性和催化活性的吡啶翁盐系列新型相转移催化剂。
成功地合成了4-二甲氨基吡啶环中N-烷基分别为正丁基、(2-乙基)己基、三苯甲基、苄基、正十二烷基的吡啶翁盐系列相转移催化剂。通过~1HNMR、mp、IR、MS对催化剂进行了结构鉴定。差热分析表明该系列催化剂具有较好的耐高温性能。
研究了该系列催化剂在芳香氯化物与KF的卤离子交换氟化反应中的催化活性，表明其具有良好的反应活性和热稳定性。通过系统地考察KF的用量、催化剂中N-烷基的结构、催化剂中阴离子的结构、反应溶剂、反应温度、芳香氯化物的不同取代基等对催化剂活性的影响等，筛选出催化活性最好的催化剂为4-二甲氨基-N-(2-乙基)己基吡啶鎓盐。在该催化剂作用下，只需反应1.5小时，对氯硝基苯氟化为对氟硝基苯的得率即可高达98.6％。
第二部分研究内容：
乙酸苄酯是一种重要的香精配料，具有新鲜果香的茉莉型香气，应用非常广
Catalysis is a useful technology in organic synthesis. Phase-transfer catalyst (PTC) has the considerable advantages, such as permitting reaction carry out under moderate condition, improving reaction rates and yields. In order to dissolve shortcomings existing in homogeneous, immobilization of PTC is one of the current interest to chemist. In this dissertation, traditional phase-transfer fluorination and solid-solid-liquid triphase-transfer esterification were studied, respectively.
The first section:
Fluorine-containing aromatic compounds are of current interest because of their special chemical and biological properties in agricultural and pharmaceutical research areas. Although a number of methods for the introducing fluorine into the organic molecules have been developed and successfully utilized for synthesis of fluoro aromatic compounds, halogen-exchange by potassium fluoride (KF) seems to be one of the most practical and useful methods. This kind of reaction must be carried out under elevated temperature.
4-(N', N'-dialkylamino) pyridinium salts are the new phase-transfer catalysts. They have higher thermal stabilities than normal pyridinum salts because of the resonance of dialkylamino and pyridine ring, which make the positive charge delocalized in multiple atoms. In this paper, a series of thermal stable PTC based on dimethylamino pyridinium salts were synthesized and characterized by ~1HNMR, mp, IR, and MS. The activities of the catalysts were evaluated in the typical aromatic nucleophilic substitution reaction (fluorination) and the excellent results were obtained.
The effects of various reaction conditions such as molar ratio of KF, structure of N-alkyl and anions, the type of substituents in substrates, reaction solvent, and temperature on the activities of catalysts were investigated in detail. Among the catalysts prepared, 4-(N', N'-dimethylamino)-N-ethylhexyl pyridinium salt (Cat2) exhibited the highest catalytic activity. It gave p-nitrofluorobenzene in yield up to
引文
[1] 徐国耀，叶志翔，精细与专用化学品，1999，20，7；
[2] 精细化学品词典，[日]精细化学品词典编辑委员会编，禹茂章等译校，化学工业出版，1989，P747；
[3] H. L. Simon, Ad. Kaufmann and H. Sehinz, Helv. Chim. Acta, 1946, 29, 1133;
[4] 化工产品手册——有机化工原料，第二版，司航主编，化学工业出版社，P605；
[5] K. G. Rutherford, W. Redmond and J. Rigamonti, J. Org. Chem., 1961, 26, 5149;
[6] E. D. Bergmann, S. Berkovic and R. Ikan, J. Am. Chem. Soc., 1956, 78, 6037;
[7] D. R. Hwang, S. M. Moerlein, L. Lang and M. J. Welch, J. Chem. Soc., Chem. Commun., 1987, 1799;
[8] H. B. Gottlieb, J. Am. Chem. Soc., 1936, 58, 532;
[9] D. J. Adams and J. H. Clark, Chem. Soc. Rev, 1999, 28, 225;
[10] H. Suzuki, N. Yazawa, Y. Yoshida, O. Furusawa and Y. Kimura, Bull. Chem. Soc. Jpn., 1990, 3, 2010;
[11] A. J. Beaumont and J. H. Clark, J. Fluorine Chem., 1993, 63, 25;
[12] M. Maggini, M. Passudetti, G. Gonzales-Trueba, M. Prato, U. Quintily and G. Scorrano, J. Org. Chem., 1991, 56, 6406;
[13] J. H. Clark, J. Fluorine Chem., 1985, 26, 2233;
[14] D. A. Wynn, Analytical Data, 1984, 30(21), 1036;
[15] 刘长令，田艳，有机氟工业，1995，4，9；
[16] Y. Sasson, M. Weiss, A. Loupy, G. Bram and C. Pardo, J. Chem. Soc., Chem. Commun., 1986, 1250;
[17] M. Yonovich-Weiss and Y. Sasson, Synthesis, 1984, 34;
[18] D. J. Brunelle, ACS Symp. Ser., 1987, 326(Phase Transfer Catal.: New Chem., Catal Appl.), 38-53;
[19] 日特开昭，58-199715(1983)；
[20] 铃本嘉一郎，桧山进，大桥雅夫，日特开昭63—10737(1988)；
[21] Y. Yoshida, Y. Kimura and M. Yomoi, Chem. Lett., 1990, 769;
[22] Y. Kimura and H. Suzuki, Tetra. Lett., 1989, 30(10), 1271;
[23] 木村芳一，有机合成化学[日]，1989，47(3)，258；
[24] N. Ishikawa, T. Kitazume, T. Yamazaki, Y. Mochida and T. Tatsuno, Chem. Lett., 1981, 61;
[25] 三木正博，滕本和元，日特开昭 63—89417(1988)；
[26] E. V. Dehrnlow and V. Knufinke, J. Chem. Res.,1989, 224;
[27] 刘增勋，陈茹玉，农药译从，1982，6，1；
[28] 王淑静，有机化学，1979，2，97；
[29] N. S. Kravchenko, V. V. Milyi, C. A., 1982, 97, 210479;
[30] G. Wittig, M. Heintzeler, Ananalen, 1947, 557, 201;
[31] M. J. arouse, Sci. Sev., 1951, 232, 1424;
[32] L. H. Sarrett, G. I. Poos, J. Am. Chem. Soc., 1953, 75, 422;
[33] G. Maerker, J. F. Carmichael, J. Org. Chem., 1961, 26, 2681;
[34] N. A. Gibson, J. W. Hosking, Aust. J. Chem., 1965, 18, 123;
[35] M. Makosza, B. Serafin, Rocz. Chem., 1965, 39, 1223;
[36] A. Brandstron, K. Oustavii, Acta. Chem. Scand., 1969, 23, 1215;
[37] C. M. Stark, J. Am. Chem. Soc., 1971, 93, 195;
[38] C. M. Stark, J. Am. Chem. Soc., 1973, 95, 3613;
[39] N. Shabestary, S. Khazadi, R. Hickman, J. of Chem. Edu. 1998, 75(11), 1470;
[40] Der-Her WANG, Hung-Shan WENG, Chem. Eng. Sci., 1995, 50, 3477;
[41] T. Tdo, T. Yamamoto, G. Jin, S. Goto, Chem. Eng. Sci., 1997, 52(20), 3511;
[42] G. Jin, T. Ido, S. Goto, Catalysis Today, 2001, 64, 279;
[43] A. W. Herriott, D. Picker, Tetra. Lett., 1972, 4521;
[44] 汪丽娜，浙江大学硕士学位论文，2002；
[45] A. W. Herriott, D. Picker, J. Am. Chem. Soc., 1975, 97, 2345;
[46] D. Landini, A. M. Maia, F. Montanari, J. Chem. Soc. Chem. Commun., 1975, 950;
[47] D. Landini, A. M. Maia, F. Montanari, J. Am. Chem. Soc., 1978, 100, 2796;
[48] Y. Sasson, O. Arrad, S. Dermeik, H. A. Zahalka, M. Weiss, H. Wiener, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 1988, 161, 495;
[49] M. Delmas, Y. L. Bigot, A. Gaset, Tetra. Lett., 1981, 21, 4831;
[50] G. Brain, A. Loupy, M. Pedoussa, Tetra. Lett., 1986, 27, 4171;
[51] R. Kelleman, R. F. Williams, G. Dimotsi, D. J. Gebri, J. C. Williams, ACS Symp. Ser. (Phase Transfer Catalysis), 1987, 326, 128;
[52] M. Tanaka, M. Koyanagy, Synthesis, 1981, 973;
[53] B. Escoula, I. Rico, A. Latles, Tetra. Lett., 1986, 27, 1499;
[54] T. Ido, T. Susaki, G. Jin, S. Goto, Applied Catalysis A: General, 2000, 201, 139;
[55] F. Miyajima, T. Iijima, M. Tomoi, Y. Kimura, React. & Funct. Polym., 2000, 43, 315;
[56] E. V. Dehmlow, S. S. Dehmlow, "Phase transfer catalyst", 1980, Verlag Chemie: W. Berlin;
[57] S. L. Regen and Y. Kimura, J. Am. Chem. Soc., 1982, 104, 2064;
[58] P. Hodge and D. C. Sherrington, "Polymer-supported reactions in organic synthesis", 1980, John Wiley, New York;
[59] 王建华，应用化学，1996，13(6)，69；
[60] 向晖，喻宗沅，应用化学，1995，12(3)，113；
[61] M. C. Vander Zwan and F. W. Harther, J. Org. Chem., 1978, 43(13), 2655;
[62] 郭锡坤，高文华，谭端明，催化学报，1997，18(6)，524；
[63] D. J. Brunelle and D. A. Singleton, Tetra. Lett., 1984, 25(32), 3383;
[64] U. Hoffmann, F. Helmer-Metzmann, M. Klapper and K. Miillen, Macromolecules, 1994, 27, 3575;
[65] U. Hoffmann, M. Klapper and K. Miillen, Polymer Bullettin, 1993, 30, 481;
[66] U. Hoffmann, F. Helmer-Metzmann, M. Klapper and K. Miillen Macromolecules, 1994, 27, 3575;
[67] G. H. Alt and J. P. Chepp U. S. 4, 371, 717(1978);
[68] F. J. Wwilliams, U. S. 4, 273, 712(1981);
[69] D. S. Johnson, U. S. 4, 163, 833(1979);
[70] W. Rieder, U. S. 4, 430, 493(1984);
[71] M. P. Mack and C. T. Berge, U. S. 4, 379, 766(1983);
[72] S. E. Callander, U. S. 4, 072, 677(1978);
[73] D. J. Brunelle and D. A. Singleton, Tetra. Lett., 1984, 25(32), 3383;
[74] Y. Yoshida and Y. Kimura, Chem. Lett., 1988, 1355;
[75] Y. Yoshida and Y. Kimura, Tetra. Lett., 1989, 30(51), 7199;
[76] H. R. Williams and H. S. Mosher, J. Am. Chem. Soc., 1954, 76, 2984;
[77] H. R. Williams and H. S. Mosher, J. Am. Chem. Soc., 1954, 76, 2987;
[78] C. S. Marvel and V. C. Sekera, Org. Synth., 1951, 20, 50;
[79] D. J. Brunelle, Daniel A. Singleton, Tetrahedron Lett., 1984, 25(32), 3383;
[80] A. V. Bhatia, S. K. Chaudhary, O. Hermandez, Org. Synth., 1998, 75, 184o
[81] R. P. Schwarzenbach, P. M. Gschwend, D. M. Imboden, Enviromental Organic Chemistry (2nd), John Wiley Sons, Inc;
[82] A．基柏里阿罗夫，有机化合物的电子理论概论，昆明医学院科研科，1975，p130；
[1] 王贵新，辽宁化工，2000，29(3)，154；
[2] J. M. Brown, J. Jenkins, J. Chem. Soc. Chem. Comm., 1976, 458;
[3] M. Cinquini, S. Colonna, H. Molinari, F. Montanari, J. Chem. Soc. Chem. Comm., 1976, 394;
[4] W. T. Ford, Adv. Polym. Sci., 1984, 55, 49;
[5] S. L. Regen, J. Org. Chem., 1979, 44(12), 1961;
[6] 刘增勋编著，相转移催化剂在有机化学和农药合成中的应用，1987，科学出版社，p333；
[7] 刘汉明，袁承业，有机化学，1983，2，123；
[8] 曾国蓉，吴朝元，西南师范大学学报，1986，3，42；
[9] S. L. Regen, J. Am. Chem. Soc., 1975, 97, 5956;
[10] S. L. Regen, J. Am. Chem. Soc., 1977, 99(2), 623;
[11] 梁逊，齐红彦，高等学校化学学报，1989，10(6)，623；
[12] 齐红彦，梁逊，催化学报，1990，11(1)，26；
[13] 冯鸣华，赵力，梁逊，离子交换与吸附，1996，12(3)，230；
[14] W. M. Mackenzie, D. C. Sherrington, Polym., 1980, 21, 791;
[15] 姜波，官月平，王靖，刘会洲，过程工程学报，2001，1(4)，382；
[16] 邱广明，孙宗华，生物化学与生物物理进展，1992，20(4)，311；
[17] C. Bergemann, D. Muller-Schulte, J. Oster, J. Magn. Magn. Mat., 1999, 194, 45;
[18] M. Koneracka, P. Kopcansky, M. Antalik, etal., J. Magn. Magn. Mat., 1999, 201, 427;
[18] 丁小斌，孙宗华，万国祥，高分子学报，2000，1，9；
[20] 陈正国，王富华，张超灿，徐羽悟，应用化学，1985，2(1)，8；
[21] J. J. Kirkland, J. J. Destefano, J. Chromatogr. Sci., 1970, 8, 309;
[22] D. C. Locke, J. Chromatogr. Sci., 1973, 11, 120;
[23] R. H. Corason, A. A. Walter, J. Chromatogr. Sci., 1971, 60, 329;
[24] 李凤艳，汪燮卿，陈拥军，李本高，应用化学，2001，18(6)，496；
[25] 李羲，赵雷康，张超灿，湖北化工，2000，2，15；
[26] J. Y. Ying, C. R Mehnert, M. S. Wong, Angew. Chem. Int. Ed., 1999, 38, 56;
[27] B. Chiche, A. Finiels, C. Gauthier, J. Org. Chem., 1989, 51, 2128;
[28] V. Paul, A. Sudalai, T. Daniel, Tetra. Lett., 1994, 35, 2601;
[29] I. Yusuke, O. Mayumi, U. Kazuo, Appl. Catal. A: Gen., 1995, 132, 127;
[30] A. Corma, M. J. Climent, H. Garcia, Appl. Catal., 1989, 49, 109;
[31] E. A. Gunnewegh, S. S. Gopie, J. Mol. Catal. A: Chem, 1996, 106, 151;
[32] R. Vasant, V. R. Choudhary, S. K. Jana, J. Catal., 2000, 192, 257;
[33] J. C. Jansen, E. J. Creyghton, S. L. Njo, Catal. Today, 1997, 38, 205;
[34] C. X. Hu, M. L. Foo, J. Catal., 2000, 195, 412;
[35] S. Jun, R. Ryoo, J. Catal., 2000, 195, 237;
[36] H. Kosslick, G. Lischke, H. Landmesser, J. Catal., 1998, 176, 102;
[37] M. J. Climent, A. Corma, J. Catalo, 1996, 161, 783;
[38] M. J. Climent, A. Corma, J. Catal., 1999, 183, 76;
[39] M. J. Climent, A. Corma, J. Catal., 1998, 175, 70;
[40] S. Janenicke, G. K. Chuah, Micro. Meso. Mater., 2000, 35-36, 143;
[41] K. nowinska, W. Kaleta, Appl. Ctal. A: Gen., 2000, 203, 91;
[42] I. Kohara, H. Fujiyama, J. Mol. Catal. A: Chem., 2000, 153, 93;
[43] M. J. Verhoef, P. J. Kooyman, J. A. Peters, Micro. Meso. Mater., 1999, 27, 365;
[44] R. D. Oldroyd, G. Sankar, J. M. Thomas, J. Phys. Chem. B., 1998, 102, 1849;
[45] G. M. Schwab, L. Rudolph, Naturwissenschaften, 1932, 20, 363;
[46] A. Baiker, Stud. Surf. Sci. Catal., 1996, 101, 51;
[47] M. A. Keane, G. Webb., J. Catal., 1992, 136, 1;
[48] U. Nagel, E. Kingel, J. Chem. Soc. Chem. Commun., 1986, 1098;
[49] A. Corma, M. Iglesias, C. P. del, J. Chem. Soc. Chem. Commun., 1991, 1253;
[50] A. Corma, M. Iglesias, J. P. Obisco, Chiral Reactions in Heterogeneous Catalysis(eds. G. Jannes, V. Dubois), New york and London: Plenum Press, 1995, 179;
[51] P. Piaggio, C. Landham, J. Chem. Soc., Perkin Trans., 2000, 143;
[52] X. G. Zhou, X. Q. Yu, Chem. Commun., 1999, 1789;
[53] G. J. Kim, J. H. Shin, Tetra. Lett., 1999, 40, 6827;
[54] S. Itsuno, J. M. J. Frechet, J. Org. Chem., 1987, 52, 4140;
[55] K. Soia, S. Niwa, M. Watanabe, J. Org. Chem., 1988, 53, 927;
[56] N. EL Mouslij, C. Caze, Eur. Polym. J., 1995, 31, 193;
[57] M. Lasperas, N. Bellocq, D. Brunel, Tetra. Asymmetry, 1998, 9, 3053;
[58] S. J. Bae, S. W. Kim, Chem. Comm., 2000, 31;
[59] B. F. G. Johnson, S. A. Raynor, Chem. Commun., 1997, 1167;
[60] S. Coman, M. Florea, Chem. Comm., 1999, 2175;
[61] R. Anwander, H. W. Gorlitzer, J. Chem. Soc. Dalton Trans., 1999, 3611;
[62] G. Gisela, P. Clemens, A. Reiner, Chem. Eur. J., 1999, 5(3), 997;
[63] B. M. Choudary, M. L. Kantam, J. Mol. Catal. A: Chem., 1999, 142, 361;
[64] I. Rodriguez, S. Iborra, A. Corma, Appl. Catal. A: Gen., 2000, 194-195, 241;
[65] R. Sercheli, R. A. Vargas, J. Mol. Catal. A: Chem., 1999, 148, 173;
[66] 周仁贤，浙江大学博士学位论文，2002；
[67] K. J. Jr. Balkus, M. Eissa, R. levado, J. Am. Chem. Soc., 1995, 117, 10753;
[68] R. F. Parton, I, F. J. Vankelecom, M. J. A. Casselman, Nature, 1994, 370, 541;
[69] R. F. Parton, P. E. Neys, P. A. Jacobs, J. Catal., 1996, 164, 341;
[70] S. Ernst, R. Glaser, M. Selle, Stud. Surf. Sci. Catal., 1997, 105, 1021;
[71] A. B. Sorokin, A. Tuel, Catal. Today, 2000, 57, 45;
[72] C. Berlini, M. Guidotti, Catal. Today, 2000, 60, 219;
[73] A. Bleloch, B. F. G. Johnson, S. V. Ley, A. J. Price, D. S. Shephard, A. W. Thomas, Chem. Commun., 1999, 1907;
[74] C. A. Koh, R. Nooney, S. Tahir, Catal. Iett., 1997, 47, 199;
[75] B. M. Choudary, M. L. Kantam, Appl. Catal. A: Gen., 1999, 181, 139;
[76] A. Cauvel, G. Renard, D. Brunel, J. Org. Chem., 1997, 62, 749;
[77] X. H. Lin, G. K. Chuah, S. Janenicke, J. Mol. Catal. A: Chem., 1999, 150, 287;
[78] S. Janenicke, G. K. Chuah, X. H. Lin, Micro. Meso. Mater., 2000, 35-36, 143;
[79] P. T. Anne, J. S. William, Synthesis, 1998, 639;
[80] A. C. Jame, W. B. Sidney, J. Org. Chem., 1984, 49, 1122;
[81] 吴文通，精细石油化工，1998，5，48；
[82] 吴文通，江西工业大学学报，1987，9，36；
[83] 张启兴，化工时刊，1993，11；
[84] G. Cainell, F. Manescalchi, Synthesis, 1975, 723;
[85] S. L. Regen, J. Am. Chem. Soc., 1975, 97(20), 5956;
[86] 陆宇，黄文强，何炳林，离子交换与吸附，1993，9(4)，359；
[87] A. Popa, Mater. Plast., 1995, 32(3-4), 1991;
[88] Yang Hui-rong, Li Bi-na, Cui Ying-de, Synth. Commun., 1998, 28(7), 1233;
[89] 黎碧娜，杨辉荣，精细化工，1998，5(6)，48；
[90] 李红缨，黎碧娜，杨辉荣，精细化工，1995，12(4)，35；
[91] 陈达美，杨辉荣，黎碧娜，廖松，张红，石油化工，1999，28(8)，528；
[92] 李凤艳，汪燮卿，陈拥军，李本高，应用化学，2001，18(6)，496；
[93] M. Tomoi, Y. Akada, H. Kakiuchi, Makromol. Chem., Rapid Commun., 1982, 3, 537;
[94] M. Tomoi, M. Goto, H. Kakiuchi, Makromol. Chem., Rapid Commun., 1985, 6, 397;
[95] 蔡明中，廖志勇，盛寿日，宋才生，有机化学，1999，19，395；
[96] 王颈松，石油与天然气化工，2002，31(1)，23；
[97] C. T. Kresge, M. E. Leonowicz, W. Roth, et al, Nature, 1992, 359, 710;
[98] J. S. Beck, J. C. Vartuli, W. J. Roth, et al, J. Am. Chem. Soc., 1992, 114(27), 10834;
[99] 黄锡文，甄寒菲，王淑兰等，应用化学，1997，14(6)，30；
[100] 张迈生，李莉，杨燕生等，中山大学学报，1998，37(2)，128；
[101] Sung-Suh Hyung Mi, Kim Dae Sung, Park Yong Ki, et al, Res. Chem. Interned., 2000, 26(3), 283;
[102] 高雄厚，毛学文，张永明等，分子催化，1997，11(5)，379；
[103] 赵修松，王清遐，徐龙伢等，催化学报，1995，16(5)，415；
[104] 孙妍，林文勇，庞文琴，霍启升，高等学校化学学报，1995，16(9)，1334；
[105] 张兆荣，索继栓，张小明等，物理化学学报，1998，14(3)，243；
[106] G. D. Stucky, A. Monier, F. Schiith, et al, Mol. Cryst. Liq. Cryst., 1994, 240, 187;
[107] L. Jiangquan, D. Tao, L. Juying, Chem. Lett., 1993, 20, 345;
[108] 董晋湘，刘光换，高瑞娟等，无机化学学报，1997，13(4)，406；
[109] 朱学文，郑淑君，廖列文，崔英德，化学推进剂与高分子材料，2002，1，24；
[110] 梅明华，杭州大学硕士学位论文，1998。
[1] P. A. Lewis, D. F. C. Morris, E. L. Short and D. N. Waters, Less-Common Metals, 1976, 45, 193;
[2] V. A. Mikhailov, Proceedings of ISEC, 1977, 1, 52;
[3] K. Inoue, Y. Baba and M. Takagi, Proceedings of ISEC 1986, 2, 65;
[4] 马恒励等，贵金属，1989，10(2)，1；
[5] 赵燮雨等，化学世界，1992，8，347；
[6] H. H. Freedman and R. A. Dubois, Tetra. Lett. 1975, 38, 3251;
[7] A. Mckillop, J. C. Fiaud and R. P. Hug, Tetra, 1974, 30, 1382;
[8] 陶凤岚等，医药工业，1982，6，12；
[9] L. A. Paquetle, W. D. Klobucar and R. A. Snow, Synth. Comm., 1976, 6, 575;
[10] 精细有机化工原料及中间体手册，徐克勋主编，化学工业出版社，p3-591；
[11] 丁金昌等，化学通报，2001，7，454；
[12] Yamin Wang and M. Koreeda, Synlett. 1996, 9, 885;
[13] F. Mohanazadeh, A. R. Momeni and Y. Ranjbar, Tetra. Lett. 1994, 35(33), 6127;
[2] 精细化学品词典，[日]精细化学品词典编辑委员会编，禹茂章等译校，化学工业出版，1989，P747；
[3] H. L. Simon, Ad. Kaufmann and H. Sehinz, Helv. Chim. Acta, 1946, 29, 1133;
[4] 化工产品手册——有机化工原料，第二版，司航主编，化学工业出版社，P605；
[5] K. G. Rutherford, W. Redmond and J. Rigamonti, J. Org. Chem., 1961, 26, 5149;
[6] E. D. Bergmann, S. Berkovic and R. Ikan, J. Am. Chem. Soc., 1956, 78, 6037;
[7] D. R. Hwang, S. M. Moerlein, L. Lang and M. J. Welch, J. Chem. Soc., Chem. Commun., 1987, 1799;
[8] H. B. Gottlieb, J. Am. Chem. Soc., 1936, 58, 532;
[9] D. J. Adams and J. H. Clark, Chem. Soc. Rev, 1999, 28, 225;
[10] H. Suzuki, N. Yazawa, Y. Yoshida, O. Furusawa and Y. Kimura, Bull. Chem. Soc. Jpn., 1990, 3, 2010;
[11] A. J. Beaumont and J. H. Clark, J. Fluorine Chem., 1993, 63, 25;
[12] M. Maggini, M. Passudetti, G. Gonzales-Trueba, M. Prato, U. Quintily and G. Scorrano, J. Org. Chem., 1991, 56, 6406;
[13] J. H. Clark, J. Fluorine Chem., 1985, 26, 2233;
[14] D. A. Wynn, Analytical Data, 1984, 30(21), 1036;
[15] 刘长令，田艳，有机氟工业，1995，4，9；
[16] Y. Sasson, M. Weiss, A. Loupy, G. Bram and C. Pardo, J. Chem. Soc., Chem. Commun., 1986, 1250;
[17] M. Yonovich-Weiss and Y. Sasson, Synthesis, 1984, 34;
[18] D. J. Brunelle, ACS Symp. Ser., 1987, 326(Phase Transfer Catal.: New Chem., Catal Appl.), 38-53;
[19] 日特开昭，58-199715(1983)；
[20] 铃本嘉一郎，桧山进，大桥雅夫，日特开昭63—10737(1988)；
[21] Y. Yoshida, Y. Kimura and M. Yomoi, Chem. Lett., 1990, 769;
[22] Y. Kimura and H. Suzuki, Tetra. Lett., 1989, 30(10), 1271;
[23] 木村芳一，有机合成化学[日]，1989，47(3)，258；
[24] N. Ishikawa, T. Kitazume, T. Yamazaki, Y. Mochida and T. Tatsuno, Chem. Lett., 1981, 61;
[25] 三木正博，滕本和元，日特开昭 63—89417(1988)；
[26] E. V. Dehrnlow and V. Knufinke, J. Chem. Res.,1989, 224;
[27] 刘增勋，陈茹玉，农药译从，1982，6，1；
[28] 王淑静，有机化学，1979，2，97；
[29] N. S. Kravchenko, V. V. Milyi, C. A., 1982, 97, 210479;
[30] G. Wittig, M. Heintzeler, Ananalen, 1947, 557, 201;
[31] M. J. arouse, Sci. Sev., 1951, 232, 1424;
[32] L. H. Sarrett, G. I. Poos, J. Am. Chem. Soc., 1953, 75, 422;
[33] G. Maerker, J. F. Carmichael, J. Org. Chem., 1961, 26, 2681;
[34] N. A. Gibson, J. W. Hosking, Aust. J. Chem., 1965, 18, 123;
[35] M. Makosza, B. Serafin, Rocz. Chem., 1965, 39, 1223;
[36] A. Brandstron, K. Oustavii, Acta. Chem. Scand., 1969, 23, 1215;
[37] C. M. Stark, J. Am. Chem. Soc., 1971, 93, 195;
[38] C. M. Stark, J. Am. Chem. Soc., 1973, 95, 3613;
[39] N. Shabestary, S. Khazadi, R. Hickman, J. of Chem. Edu. 1998, 75(11), 1470;
[40] Der-Her WANG, Hung-Shan WENG, Chem. Eng. Sci., 1995, 50, 3477;
[41] T. Tdo, T. Yamamoto, G. Jin, S. Goto, Chem. Eng. Sci., 1997, 52(20), 3511;
[42] G. Jin, T. Ido, S. Goto, Catalysis Today, 2001, 64, 279;
[43] A. W. Herriott, D. Picker, Tetra. Lett., 1972, 4521;
[44] 汪丽娜，浙江大学硕士学位论文，2002；
[45] A. W. Herriott, D. Picker, J. Am. Chem. Soc., 1975, 97, 2345;
[46] D. Landini, A. M. Maia, F. Montanari, J. Chem. Soc. Chem. Commun., 1975, 950;
[47] D. Landini, A. M. Maia, F. Montanari, J. Am. Chem. Soc., 1978, 100, 2796;
[48] Y. Sasson, O. Arrad, S. Dermeik, H. A. Zahalka, M. Weiss, H. Wiener, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 1988, 161, 495;
[49] M. Delmas, Y. L. Bigot, A. Gaset, Tetra. Lett., 1981, 21, 4831;
[50] G. Brain, A. Loupy, M. Pedoussa, Tetra. Lett., 1986, 27, 4171;
[51] R. Kelleman, R. F. Williams, G. Dimotsi, D. J. Gebri, J. C. Williams, ACS Symp. Ser. (Phase Transfer Catalysis), 1987, 326, 128;
[52] M. Tanaka, M. Koyanagy, Synthesis, 1981, 973;
[53] B. Escoula, I. Rico, A. Latles, Tetra. Lett., 1986, 27, 1499;
[54] T. Ido, T. Susaki, G. Jin, S. Goto, Applied Catalysis A: General, 2000, 201, 139;
[55] F. Miyajima, T. Iijima, M. Tomoi, Y. Kimura, React. & Funct. Polym., 2000, 43, 315;
[56] E. V. Dehmlow, S. S. Dehmlow, "Phase transfer catalyst", 1980, Verlag Chemie: W. Berlin;
[57] S. L. Regen and Y. Kimura, J. Am. Chem. Soc., 1982, 104, 2064;
[58] P. Hodge and D. C. Sherrington, "Polymer-supported reactions in organic synthesis", 1980, John Wiley, New York;
[59] 王建华，应用化学，1996，13(6)，69；
[60] 向晖，喻宗沅，应用化学，1995，12(3)，113；
[61] M. C. Vander Zwan and F. W. Harther, J. Org. Chem., 1978, 43(13), 2655;
[62] 郭锡坤，高文华，谭端明，催化学报，1997，18(6)，524；
[63] D. J. Brunelle and D. A. Singleton, Tetra. Lett., 1984, 25(32), 3383;
[64] U. Hoffmann, F. Helmer-Metzmann, M. Klapper and K. Miillen, Macromolecules, 1994, 27, 3575;
[65] U. Hoffmann, M. Klapper and K. Miillen, Polymer Bullettin, 1993, 30, 481;
[66] U. Hoffmann, F. Helmer-Metzmann, M. Klapper and K. Miillen Macromolecules, 1994, 27, 3575;
[67] G. H. Alt and J. P. Chepp U. S. 4, 371, 717(1978);
[68] F. J. Wwilliams, U. S. 4, 273, 712(1981);
[69] D. S. Johnson, U. S. 4, 163, 833(1979);
[70] W. Rieder, U. S. 4, 430, 493(1984);
[71] M. P. Mack and C. T. Berge, U. S. 4, 379, 766(1983);
[72] S. E. Callander, U. S. 4, 072, 677(1978);
[73] D. J. Brunelle and D. A. Singleton, Tetra. Lett., 1984, 25(32), 3383;
[74] Y. Yoshida and Y. Kimura, Chem. Lett., 1988, 1355;
[75] Y. Yoshida and Y. Kimura, Tetra. Lett., 1989, 30(51), 7199;
[76] H. R. Williams and H. S. Mosher, J. Am. Chem. Soc., 1954, 76, 2984;
[77] H. R. Williams and H. S. Mosher, J. Am. Chem. Soc., 1954, 76, 2987;
[78] C. S. Marvel and V. C. Sekera, Org. Synth., 1951, 20, 50;
[79] D. J. Brunelle, Daniel A. Singleton, Tetrahedron Lett., 1984, 25(32), 3383;
[80] A. V. Bhatia, S. K. Chaudhary, O. Hermandez, Org. Synth., 1998, 75, 184o
[81] R. P. Schwarzenbach, P. M. Gschwend, D. M. Imboden, Enviromental Organic Chemistry (2nd), John Wiley Sons, Inc;
[82] A．基柏里阿罗夫，有机化合物的电子理论概论，昆明医学院科研科，1975，p130；
[1] 王贵新，辽宁化工，2000，29(3)，154；
[2] J. M. Brown, J. Jenkins, J. Chem. Soc. Chem. Comm., 1976, 458;
[3] M. Cinquini, S. Colonna, H. Molinari, F. Montanari, J. Chem. Soc. Chem. Comm., 1976, 394;
[4] W. T. Ford, Adv. Polym. Sci., 1984, 55, 49;
[5] S. L. Regen, J. Org. Chem., 1979, 44(12), 1961;
[6] 刘增勋编著，相转移催化剂在有机化学和农药合成中的应用，1987，科学出版社，p333；
[7] 刘汉明，袁承业，有机化学，1983，2，123；
[8] 曾国蓉，吴朝元，西南师范大学学报，1986，3，42；
[9] S. L. Regen, J. Am. Chem. Soc., 1975, 97, 5956;
[10] S. L. Regen, J. Am. Chem. Soc., 1977, 99(2), 623;
[11] 梁逊，齐红彦，高等学校化学学报，1989，10(6)，623；
[12] 齐红彦，梁逊，催化学报，1990，11(1)，26；
[13] 冯鸣华，赵力，梁逊，离子交换与吸附，1996，12(3)，230；
[14] W. M. Mackenzie, D. C. Sherrington, Polym., 1980, 21, 791;
[15] 姜波，官月平，王靖，刘会洲，过程工程学报，2001，1(4)，382；
[16] 邱广明，孙宗华，生物化学与生物物理进展，1992，20(4)，311；
[17] C. Bergemann, D. Muller-Schulte, J. Oster, J. Magn. Magn. Mat., 1999, 194, 45;
[18] M. Koneracka, P. Kopcansky, M. Antalik, etal., J. Magn. Magn. Mat., 1999, 201, 427;
[18] 丁小斌，孙宗华，万国祥，高分子学报，2000，1，9；
[20] 陈正国，王富华，张超灿，徐羽悟，应用化学，1985，2(1)，8；
[21] J. J. Kirkland, J. J. Destefano, J. Chromatogr. Sci., 1970, 8, 309;
[22] D. C. Locke, J. Chromatogr. Sci., 1973, 11, 120;
[23] R. H. Corason, A. A. Walter, J. Chromatogr. Sci., 1971, 60, 329;
[24] 李凤艳，汪燮卿，陈拥军，李本高，应用化学，2001，18(6)，496；
[25] 李羲，赵雷康，张超灿，湖北化工，2000，2，15；
[26] J. Y. Ying, C. R Mehnert, M. S. Wong, Angew. Chem. Int. Ed., 1999, 38, 56;
[27] B. Chiche, A. Finiels, C. Gauthier, J. Org. Chem., 1989, 51, 2128;
[28] V. Paul, A. Sudalai, T. Daniel, Tetra. Lett., 1994, 35, 2601;
[29] I. Yusuke, O. Mayumi, U. Kazuo, Appl. Catal. A: Gen., 1995, 132, 127;
[30] A. Corma, M. J. Climent, H. Garcia, Appl. Catal., 1989, 49, 109;
[31] E. A. Gunnewegh, S. S. Gopie, J. Mol. Catal. A: Chem, 1996, 106, 151;
[32] R. Vasant, V. R. Choudhary, S. K. Jana, J. Catal., 2000, 192, 257;
[33] J. C. Jansen, E. J. Creyghton, S. L. Njo, Catal. Today, 1997, 38, 205;
[34] C. X. Hu, M. L. Foo, J. Catal., 2000, 195, 412;
[35] S. Jun, R. Ryoo, J. Catal., 2000, 195, 237;
[36] H. Kosslick, G. Lischke, H. Landmesser, J. Catal., 1998, 176, 102;
[37] M. J. Climent, A. Corma, J. Catalo, 1996, 161, 783;
[38] M. J. Climent, A. Corma, J. Catal., 1999, 183, 76;
[39] M. J. Climent, A. Corma, J. Catal., 1998, 175, 70;
[40] S. Janenicke, G. K. Chuah, Micro. Meso. Mater., 2000, 35-36, 143;
[41] K. nowinska, W. Kaleta, Appl. Ctal. A: Gen., 2000, 203, 91;
[42] I. Kohara, H. Fujiyama, J. Mol. Catal. A: Chem., 2000, 153, 93;
[43] M. J. Verhoef, P. J. Kooyman, J. A. Peters, Micro. Meso. Mater., 1999, 27, 365;
[44] R. D. Oldroyd, G. Sankar, J. M. Thomas, J. Phys. Chem. B., 1998, 102, 1849;
[45] G. M. Schwab, L. Rudolph, Naturwissenschaften, 1932, 20, 363;
[46] A. Baiker, Stud. Surf. Sci. Catal., 1996, 101, 51;
[47] M. A. Keane, G. Webb., J. Catal., 1992, 136, 1;
[48] U. Nagel, E. Kingel, J. Chem. Soc. Chem. Commun., 1986, 1098;
[49] A. Corma, M. Iglesias, C. P. del, J. Chem. Soc. Chem. Commun., 1991, 1253;
[50] A. Corma, M. Iglesias, J. P. Obisco, Chiral Reactions in Heterogeneous Catalysis(eds. G. Jannes, V. Dubois), New york and London: Plenum Press, 1995, 179;
[51] P. Piaggio, C. Landham, J. Chem. Soc., Perkin Trans., 2000, 143;
[52] X. G. Zhou, X. Q. Yu, Chem. Commun., 1999, 1789;
[53] G. J. Kim, J. H. Shin, Tetra. Lett., 1999, 40, 6827;
[54] S. Itsuno, J. M. J. Frechet, J. Org. Chem., 1987, 52, 4140;
[55] K. Soia, S. Niwa, M. Watanabe, J. Org. Chem., 1988, 53, 927;
[56] N. EL Mouslij, C. Caze, Eur. Polym. J., 1995, 31, 193;
[57] M. Lasperas, N. Bellocq, D. Brunel, Tetra. Asymmetry, 1998, 9, 3053;
[58] S. J. Bae, S. W. Kim, Chem. Comm., 2000, 31;
[59] B. F. G. Johnson, S. A. Raynor, Chem. Commun., 1997, 1167;
[60] S. Coman, M. Florea, Chem. Comm., 1999, 2175;
[61] R. Anwander, H. W. Gorlitzer, J. Chem. Soc. Dalton Trans., 1999, 3611;
[62] G. Gisela, P. Clemens, A. Reiner, Chem. Eur. J., 1999, 5(3), 997;
[63] B. M. Choudary, M. L. Kantam, J. Mol. Catal. A: Chem., 1999, 142, 361;
[64] I. Rodriguez, S. Iborra, A. Corma, Appl. Catal. A: Gen., 2000, 194-195, 241;
[65] R. Sercheli, R. A. Vargas, J. Mol. Catal. A: Chem., 1999, 148, 173;
[66] 周仁贤，浙江大学博士学位论文，2002；
[67] K. J. Jr. Balkus, M. Eissa, R. levado, J. Am. Chem. Soc., 1995, 117, 10753;
[68] R. F. Parton, I, F. J. Vankelecom, M. J. A. Casselman, Nature, 1994, 370, 541;
[69] R. F. Parton, P. E. Neys, P. A. Jacobs, J. Catal., 1996, 164, 341;
[70] S. Ernst, R. Glaser, M. Selle, Stud. Surf. Sci. Catal., 1997, 105, 1021;
[71] A. B. Sorokin, A. Tuel, Catal. Today, 2000, 57, 45;
[72] C. Berlini, M. Guidotti, Catal. Today, 2000, 60, 219;
[73] A. Bleloch, B. F. G. Johnson, S. V. Ley, A. J. Price, D. S. Shephard, A. W. Thomas, Chem. Commun., 1999, 1907;
[74] C. A. Koh, R. Nooney, S. Tahir, Catal. Iett., 1997, 47, 199;
[75] B. M. Choudary, M. L. Kantam, Appl. Catal. A: Gen., 1999, 181, 139;
[76] A. Cauvel, G. Renard, D. Brunel, J. Org. Chem., 1997, 62, 749;
[77] X. H. Lin, G. K. Chuah, S. Janenicke, J. Mol. Catal. A: Chem., 1999, 150, 287;
[78] S. Janenicke, G. K. Chuah, X. H. Lin, Micro. Meso. Mater., 2000, 35-36, 143;
[79] P. T. Anne, J. S. William, Synthesis, 1998, 639;
[80] A. C. Jame, W. B. Sidney, J. Org. Chem., 1984, 49, 1122;
[81] 吴文通，精细石油化工，1998，5，48；
[82] 吴文通，江西工业大学学报，1987，9，36；
[83] 张启兴，化工时刊，1993，11；
[84] G. Cainell, F. Manescalchi, Synthesis, 1975, 723;
[85] S. L. Regen, J. Am. Chem. Soc., 1975, 97(20), 5956;
[86] 陆宇，黄文强，何炳林，离子交换与吸附，1993，9(4)，359；
[87] A. Popa, Mater. Plast., 1995, 32(3-4), 1991;
[88] Yang Hui-rong, Li Bi-na, Cui Ying-de, Synth. Commun., 1998, 28(7), 1233;
[89] 黎碧娜，杨辉荣，精细化工，1998，5(6)，48；
[90] 李红缨，黎碧娜，杨辉荣，精细化工，1995，12(4)，35；
[91] 陈达美，杨辉荣，黎碧娜，廖松，张红，石油化工，1999，28(8)，528；
[92] 李凤艳，汪燮卿，陈拥军，李本高，应用化学，2001，18(6)，496；
[93] M. Tomoi, Y. Akada, H. Kakiuchi, Makromol. Chem., Rapid Commun., 1982, 3, 537;
[94] M. Tomoi, M. Goto, H. Kakiuchi, Makromol. Chem., Rapid Commun., 1985, 6, 397;
[95] 蔡明中，廖志勇，盛寿日，宋才生，有机化学，1999，19，395；
[96] 王颈松，石油与天然气化工，2002，31(1)，23；
[97] C. T. Kresge, M. E. Leonowicz, W. Roth, et al, Nature, 1992, 359, 710;
[98] J. S. Beck, J. C. Vartuli, W. J. Roth, et al, J. Am. Chem. Soc., 1992, 114(27), 10834;
[99] 黄锡文，甄寒菲，王淑兰等，应用化学，1997，14(6)，30；
[100] 张迈生，李莉，杨燕生等，中山大学学报，1998，37(2)，128；
[101] Sung-Suh Hyung Mi, Kim Dae Sung, Park Yong Ki, et al, Res. Chem. Interned., 2000, 26(3), 283;
[102] 高雄厚，毛学文，张永明等，分子催化，1997，11(5)，379；
[103] 赵修松，王清遐，徐龙伢等，催化学报，1995，16(5)，415；
[104] 孙妍，林文勇，庞文琴，霍启升，高等学校化学学报，1995，16(9)，1334；
[105] 张兆荣，索继栓，张小明等，物理化学学报，1998，14(3)，243；
[106] G. D. Stucky, A. Monier, F. Schiith, et al, Mol. Cryst. Liq. Cryst., 1994, 240, 187;
[107] L. Jiangquan, D. Tao, L. Juying, Chem. Lett., 1993, 20, 345;
[108] 董晋湘，刘光换，高瑞娟等，无机化学学报，1997，13(4)，406；
[109] 朱学文，郑淑君，廖列文，崔英德，化学推进剂与高分子材料，2002，1，24；
[110] 梅明华，杭州大学硕士学位论文，1998。
[1] P. A. Lewis, D. F. C. Morris, E. L. Short and D. N. Waters, Less-Common Metals, 1976, 45, 193;
[2] V. A. Mikhailov, Proceedings of ISEC, 1977, 1, 52;
[3] K. Inoue, Y. Baba and M. Takagi, Proceedings of ISEC 1986, 2, 65;
[4] 马恒励等，贵金属，1989，10(2)，1；
[5] 赵燮雨等，化学世界，1992，8，347；
[6] H. H. Freedman and R. A. Dubois, Tetra. Lett. 1975, 38, 3251;
[7] A. Mckillop, J. C. Fiaud and R. P. Hug, Tetra, 1974, 30, 1382;
[8] 陶凤岚等，医药工业，1982，6，12；
[9] L. A. Paquetle, W. D. Klobucar and R. A. Snow, Synth. Comm., 1976, 6, 575;
[10] 精细有机化工原料及中间体手册，徐克勋主编，化学工业出版社，p3-591；
[11] 丁金昌等，化学通报，2001，7，454；
[12] Yamin Wang and M. Koreeda, Synlett. 1996, 9, 885;
[13] F. Mohanazadeh, A. R. Momeni and Y. Ranjbar, Tetra. Lett. 1994, 35(33), 6127;
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