跳到主要內容

臺灣博碩士論文加值系統

(100.28.2.72) 您好!臺灣時間:2024/06/22 21:00
字體大小: 字級放大   字級縮小   預設字形  
回查詢結果 :::

詳目顯示

我願授權國圖
: 
twitterline
研究生:薛茂霖
研究生(外文):Mao-Lin Hsueh
論文名稱:含雙氧配位基EDBP之鋰、鈉、鎂及鋅化合物之合成、鑑定及其於開環聚合與陰離子 聚合反應之催化研究
論文名稱(外文):Synthesis, Characterization and Catalytic Studies of EDBP Supported Lithium, Sodium, Magnesium and Zinc Complexes: Efficient Catalysts for Ring-Opening Polymerization of e-Caprolactone and L-Lactide and Anionic Polymerization of Methyl Methacrylate
指導教授:林助傑
口試委員:高漢謀洪豐裕陳繼添葉玉堂柯寶燦
口試日期:2006-07-12
學位類別:博士
校院名稱:國立中興大學
系所名稱:化學系所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2006
畢業學年度:94
語文別:中文
論文頁數:111
中文關鍵詞:開環聚合環己內酯乳酸交酯陰離子聚合甲基丙烯酸甲酯
外文關鍵詞:lithiummagensiunsodiumzincring-opening polymerizationcaprolactonelactideanionic polymerizationmethyl methacrylate
相關次數:
  • 被引用被引用:0
  • 點閱點閱:7
  • 評分評分:
  • 下載下載:0
  • 收藏至我的研究室書目清單書目收藏:0
Several novel zinc and magnesium aryloxides, [(EDBP)Zn(THF)]2 (1), [(EDBP)Mg(Et2O)]2 (2), and [(EDBP)Mg(THF)]2 (3), have been synthesized by the reaction of 2,2¢-ethylidenebis(4,6-di-tert-butylphenol) (EDBP-H2) with ZnEt2 or MgnBu2 in diethyl ether (Et2O) or tetrahydrofuran (THF), respectively. Experimental results show that 1-3 efficiently catalyze the ring-opening polymerization (ROP) of e-caprolactone (e-CL) and L-lactide (L-LA) in a controlled fashion, yielding polymers with very narrow polydispersity indexes (PDI) in a wide range of monomer-to-initiator ratios. The reaction of EDBP-H2 with nBuLi in THF, Et2O or hexane, gives [(EDBP-H)Li(THF)3] (4), [(EDBP-H)Li(Et2O)3] (5) or [(EDBP-H)Li]3 (6), respectively. However, the reaction of EDBP-H2 with nBuLi in the presence of benzyl alcohol (BnOH) in Et2O or THF produces compound [(EDBP-H)Li(BnOH)]2 (7) or [(EDBP-H)Li(BnOH)(THF)2] (8), respectively. Further reaction of 7 with excess of THF produces 8. Alternatively, 8 can also be prepared by the reaction of benzyl alcohol with 4 in toluene. Experimental results show that 7 and 8 efficiently initiate the ROP of L-lactide in a controlled fashion, yielding polymers with very narrow polydispersity indexes in a wide range of monomer-to-initiator ratios. Moreover, the reaction of EDBP-H2 with 2.2 equiv nBuLi in Et2O affords [(EDBP)Li2(Et2O)]2 (9). Moreover, block copolymers, polystyrene-b-poly(L-lactide), have also been prepared from the ring-opening polymerization of L-latide catalyzed by 2 and 4 using polystyrene as a macroinitiator.
The unusual lithium n-butylmagnesium [(EDBP)Mg(m2-nBu)Li(Et2O)]2 (10), sodium n-butylmagnesium [(EDBP)Na(Et2O)MgnBu]2 (13), lithium ethylzinc [(EDBP)Zn(THF)]2[(m2-C2H5)Li(THF)] (14) and lithium-magnesium enolate, {(EDBP)Mg[m2-OC(Mes)CH2]Li(Et2O)}2 (11), and the sodium aggregate, [(EDBP)Na2]4 (12), have been synthesized and structurally characterized. Among them, 10, 11, 13 and 14 have been used as initiators for the polymerization of methyl methacrylate. The dimeric lithium n-butylmagnesium complex 10 was obtained from the reaction of [(EDBP)Li(Et2O)3] (5) with a stoichiometric amount of MgnBu2. Alternatively, 10 can also be prepared by the reaction of [(EDBP)Mg(Et2O)]2 (2) with a stoichiometric amount of nBuLi in Et2O. Furthermore, the reaction of 10 with 2¢,4¢,6¢-trimethylacetophenone (MesC(O)CH3, Mes = 2,4,6-Me3C6H2) produces 11. Reaction of EDBP-H2 with excess sodium metal in Et2O furnishes compound 12. In the presence of a stoichiometric amount of MgnBu2 in Et2O, 12 can be converted to the dimeric sodium-magnesium mixed-metal complex [(EDBP)Na(Et2O)MgnBu]2 (13). Moreover, 14 can be obtained by the reaction of [(EDBP)Li(THF)3] (4) with a stoichiometric amount of ZnEt2. Experimental results show that 10, 11, 13 and 14 efficiently initiate the anionic polymerization of methyl methacrylate.
Abstract…………………………………………………………………....1
Chapter 1. Introduction
Biodegradable Polymers……………………………………....3
Metal Complexes Supported by Salen Ligands………………5
Metal Complexes Supported by Biphenol Ligands…………...8
References…………………………………………………...11
Chapter 2. Zinc, Magnesium and Lithium Complexes
Introduction……………………………………………....….15
Results and Discussion………………………………………17
Synthesis and Spectroscopic Studies of Compounds1-9…....17
Molecular Structure Studies of 1-3………………………….20
Molecular Structure Studies of 4 and 6-9……………….…..24
ROP of e-CL Using Complex 1 as Initiator………………...33
ROP of L-LA Using Complexes 1-3 as catalysts………......37
Proposed Mechanism for ROP of L-LA Catalyzed by 1-3...44
ROP of L-LA Using Complexes 7 and 8 as Initiators…….....46
Proposed Mechanism for ROP of L-LA Catalyzed by 7…...50
Summary………...…………………………..……………....52
Experimental Section…………………………………..…....52
References………………………………..………………….58
Chapter 3. Application for the Synthesis of PS-b-PLLA
Introduction………………………………………………….62
Preparation of 4-Hydroxyl-TEMPO-terminated Polystyrene
…………………………………………………………….…64
Synthesis of Polystyrene-Poly(L-lactide) Diblock Copolymer
……………………………………………………....…...….67
Summary…...…………………………………………..…....70
Experimental Section…………………………………..…....70
References………………………………..………...………..71
Chapter 4. Mixed- Metal Complexes
Introduction………………………………………………….73
Results and Discussion……………………………………....81
Synthesis and Spectroscopic Studies of 10-14……………...81
Molecular structure studies of 10-14………………………..83
Polymerization of MMA Using Complexes 10, 11, 13 and 14 as Initiators…………………………………………………..93
Summary………………………….…..……………………..97
Experimental Section………………………………………..97
References………………………………………………….100
Chapter 5. Conclusion………………………………………………….106
Chapter 6. General Informations
NMR Spectra…………………………………....………….109
Gel Permeation Chromatography (GPC)…………………..109
X-ray Crystallographic Studies………..…..…………...….109
Differential Scanning Calorimeter (DSC)…………...…......110
Materials…………………………………………………....110
Reference…………………………………..….……….…...111

Catalog of Scheme, Figures and Tables

Scheme 1…………………………………………………………….……18
Scheme 2……………………………………………………………….…45
Scheme 3……………………………………………………………….…51
Scheme 4………………………………………………………………….66
Scheme 5………………………………………………………………….82
Scheme 6……………………………………………………………...…108

Figure 1…………………………………………………………………....21
Figure 2…………………………………………………………………....21
Figure 3……………………………………………………………………25
Figure 4……………………………………………………………………25
Figure 5……………………………………………………………………29
Figure 6……………………………………………………………………29
Figure 7……………………………………………………………………32
Figure 8…………………………………………………………………....36
Figure 9……………………………………………………………………37
Figure 10…………………………………………………………………..42
Figure 11…………………………………………………………………..43
Figure 12…………………………………………………………………..49
Figure 13……………………………………………………………….….49
Figure 14…………………………………………………………………..69
Figure 15…………………………………………………………………..69
Figure 16…………………………………………………………………..85
Figure 17…………………………………………………………………..86
Figure 18…………………………………………………………………..86
Figure 19…………………………………………………………………..87
Figure 20…………………………………………………………………..87
Figure 21…………………………………………………………………..96

Table 1…………………………………………………………………….22 Table 2…………………………………………………………………….22
Table 3…………………………………………………………………….23
Table 4…………………………………………………………………….26
Table 5…………………………………………………………………….26
Table 6…………………………………………………………………….27
Table 7…………………………………………………………………….30
Table 8…………………………………………………………………….30
Table 9…………………………………………………………………….31
Table 10…………………………………………………………………...33
Table 11…………………………………………………………………...35
Table 12…………………………………………………………….…..…40
Table 13………………………………………………………………...…41
Table 14……………………………………………………….…………..48
Table 15………………………………………………………………...…66
Table 16………………………………………………………………...…68
Table 17………………………………………………………………...…88
Table 18………………………………………………………………..….88
Table 19………………………………………………………………...…89
Table 20………………………………………………………………..…90
Table 21………………………………………………………………..…91
Table 22………………………………………………………………..…92
Table 23………………………………………………………………..…95
References

1.(a) Seift, G. Acc. Chem. Res. 1993, 26, 105. (b) Fujisato, T.; Ikada, Y. Macromol. Symp. 1996, 103, 73. (c) Hutchinson, F. G.; Furr, B. J. A. In High Value Polymers; Fawcett, A. H. Ed.; The Royal Society of Chemistry: Science Park, Cambridge.
2.Piskin, E. J. Biomater. Sci. Polym. Ed. 1995, 6, 775.
3.Shalaby, S. W. Biomedical Polymers; Hanser: New York, 1994.
4.Chamberlain, B. M.; Sun, Y.; Hagadorn, J. R.; Hemmesch, E. W.; Young, Jr.; V. G.; Pink, M.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400.
5.(a) Endo, M.; Aida, T.; Inoue, S. Macromolecules 1987, 20, 2982. (b) Dudat, A.; Florjanczyk, Z.; Hofman, A.; Slomkowski, S.; Penczek, S. Macromolecules 1990, 23, 1640. (c) Kowalski, A.; Duda, A.; Penczek, S.; Macromol. Rapid. Commun. 1998, 19, 567. (d) Gan, Z.; Jim, T. F.; Jim, M.; Yuer, Z.; Wang, S.; Wu, C. Macromolcules 1999, 32, 1218.
6.(a) Hovestadt, W.; Muller, J. A.; Hocker, H. Macromol. Chem. Rapid. Commun. 1990, 11, 271. (b) Hovestadt, W.; Keul, H.; Hocker, H. Polymer 1992, 33, 1941.
7.(a) Uhrich, K. E. et al. Chem. Rev. 1999, 99, 3181. (b) Dobrzynski, P. et al. Macromolecules 1999, 32, 4735.
8.The PDI is the weight average molecular weight divided by number average molecular weight (Mw/Mn) and is often determined by gel permeation chromatography (GPC). For reference, the standard deviation (s) of a molecular weight distribution is given by: s = Mn (PDI-1)1/2.
9.(a) Endo, M.; Aida, T.; Inoue, S. Macromolecules 1987, 20, 2982. (b) Duda, A.; Florjanczyk, Z.; Hofman, A.; Slomkowski, S.; Penczek, S. Macromolecules 1990, 23, 1640. (c) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39. (d) Kowalski, A.; Duda, A.; Penczek, S. Macromol. Rapid Commun. 1998, 19, 567. (e) Ko, B. T.; Lin, C. C. Macromolecules 1999, 32, 8296.
10. (a) Dittrich, W.; Schulz, R. C. Angew. Makromol. Chem. 1971, 15, 109. (b) Aida, T. Prog. Polym. Sci. 1994, 19, 469. (c) Cheng, M.; Attygalle, A. B.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 11583. (d) Chamberlain, B. M.; Cheng, M.; Moore, D. R.; Ovitt, T. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 3229.
11.(a) Kim, S. H.; Han, Y. K.; Kim, Y. H.; Hong, S. I. Makromol. Chem. 1992, 193, 1623. (b) Sawhney, A.; Pathak, C. P.; Hubbell, J. A. Macromolecules 1993, 26, 581. (c) Zhang, X.; MacDonald, D. A.; Goosen, M. F. A.; McAuley, K. B. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 2965. (d) Han, D. K.; Hubbell, J. A. Macromolecules 1996, 29, 5233. (e) Kricheldorf, H. R.; Kreiser-Saunders: I.; Stricker, A. Macromolecules 2000, 33, 702.
12.(a) McLain, S. J.; Ford, T. M.; Drysdale, N. E. Polym. Prepr. (Am Chem. Soc., Div. Polym. Chem.) 1992, 33, 463. (b) Leborgne, A.; Pluta, C.; Spassky, N. Macromol. Rapid Commun. 1994, 15, 955. (c) Stevels, W. M.; Ankone, M. T.; Dijkstra, P. J.; Feijen, J. Macromolecules 1996, 29, 3332. (d) Li, S. M.; Rashkov, I.; Espartero, L.; Manolova, N.; Vert, M. Macromolecules 1996, 29, 57.
13.(a) Jedlinski, Z.; Walach, W. Makromol. Chem. 1991, 192, 2051. (b) Chamberlain, B. M.; Sun, Y.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G., Jr.; Pink, M.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400. (c) Simic, V.; Spassky, N.; Hubert-Pfalzgraf, I. G. Macromolecules 1997, 30, 7338. (d) Deng, X.; Yuan, M.; Xiong, C.; Li, X. J. Appl. Polym. Sci. 1999, 73, 1401. (e) Li, S. M.; Rashkov, I.; Espartero, L.; Manolova, N.; Vert, M. Macromolecules 1996, 29, 57.
14.(a) Ko, B. T.; Lin, C. C. J. Am. Chem. Soc. 2001, 123, 7973. (b) Yu, T. L.; Wu, C. C.; Chen, C. C.; Huang, B. H.; Wu, J. C.; Lin, C.C. Polymer 2005, 46, 5905.
14.(a) Ouhadi, T. et. al. Makromol. Chem. Suppl. 1975, 1, 191. (b)Ouhadi, T. et. al. Macromolecules 1991, 24, 2266.
16.(a) Bhaw-Luximon, A.; Jhurry, D.; Spassky, N. Polymer Bulletin 2000, 44, 31. (b) Cameron, P. A.; Jhurry, D.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; Williams, S. Macromol. Rapid Commun. 1999, 20, 616. (c) Jhurry, D.; Bhaw-Luximon, A.; Spassky, N. Macromol.Symp. 2001, 175, 67.
17.Montaudo, G.; Montaudo, M. S.; Puglisi, C.; Samperi, F.; Spassky, N.; LeBorgne, A.; Wisniewski, M. Macromolecules 1996, 29, 6461.
18.Chisholm, M. H.; Lin, C. C.; Gallucci, J. C.; Ko, B. T. Dalton Trans. 2003, 406.
19.(a) Prakasha, T. K.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1993, 115, 2690. (b) Nakayama, Y.; Watanabe, K.; Ueyama, N.; Nakamura, A.; Harada, A.; Okuda, J. Organometallics 2000, 19, 2498. (c) Takashima, Y.; Nakayama, Y.; Watanabe, K.; Itono, T.; eyama, N.; Nakamura, A.; Yasuda, H.; Harada, A. Macromolecules 2002, 35, 7538. (d) Takashima, Y.; Nakayama, Y.; Hirao, T.; Yasuda, H.; Harada, A. J. Organomet. Chem. 2004, 689, 612.
20.(a) Ko, B. T.; Woo, C. C.; Lin, C. C. Organometallics 2000, 19, 1864. (b) Chen, H. L.; Ko, B. T.; Huang, B. H.; Lin, C. C. Organometallics 2001, 20, 5076. (c) Liu, Y. C.; Ko, B.T.; Lin, C. C. Macromolecules 2001, 34, 6196. (d) Hsueh, M. L.; Huang, B. H.; Lin, C. C. Macromolecules 2002, 35, 5763.
References
1.(a) Fujisato, T.; Ikada, Y. Macromol. Symp. 1996, 103, 73. (b) Hutchinson, F. G.; Furr, B. J. A. In High Value Polymers; Fawcett. A. H., Ed.; The Royal Society of Chemistry: Science Park, Cambridge. (c) Swift, G. Acc. Chem. Res. 1993, 26, 105.
2.(a) Jeong, B.; Bae, Y. H.; Lee, D. S.; Kim, S. W. Nature (London) 1997, 388, 860. (b) Gref, R.; Minamitake, Y.; Peracchia, M. T.; Trubetskov, V.; Torchilin, V.; Langer, R. Science 1994, 263, 1600. (c) Fujisato, T.; Ikada, Y. Macromol. Symp. 1996, 103, 73. (d) Pitt, C. G., Schindler, A. Biodegradable and Delivery Systems for Contraception, Progress in Contraceptive Delivery Systems, 1st ed.; MTP Press: Lancaster, U.K., 1980; p 17. (e) Domb, A. J.; Kost, J.; Wiseman, D. M. Handbook of Biodegradable Polymers, 1st ed.; Harwood Academic Publishers: Amsterdam, 1997; p 3.
3.(a) Endo, M.; Aida, T.; Inoue, S. Macromolecules 1987, 20, 2982. (b) Duda, A.; Florjanczyk, Z.; Hofman, A.; Slomkowski, S.; Penczek, S. Macromolecules 1990, 23, 1640. (c) Aida, T.; Inoue, S. Acc. Chem. Res. 1996, 29, 39. (d) Kowalski, A.; Duda, A.; Penczek, S. Macromol. Rapid Commun. 1998, 19, 567. (e) Ko, B. T.; Lin, C. C. Macromolecules 1999, 32, 8296.
4.(a) Ko, B. T.; Lin, C. C. Macromolecules 1999, 32, 8296. (b) Liu, Y. C.; Ko, B. T.; Lin, C. C. Macromolecules 2001, 34, 6196. (c) Hsueh, M. L.; Huang, B. H.; Lin, C. C. Macromolecules 2002, 35, 5763.
5.(a) Ko, B. T.; Lin, C. C. J. Am. Chem. Soc. 2001, 123, 7973. (b) Kricheldorf, H. R.; Saunders, K. Makromol. Chem. 1990, 191, 1057-1066. (c) Kasperczyk, J. E.; Bero, M. Polymer 2000, 41, 391. (d) Kasperczyk, J. E. Macromolecules 1995, 28, 3937. (e) Xie, W.; Chen, D.; Fan, X.; Li, J.; Wang, P.; Cheng, H. N.; Nickol, R. G. J. Polym. Sci.: Part A, Polym. Chem. 1999, 37, 3486.
6.(a) Dittrich, W.; Schulz, R. C. Angew. Makromol. Chem. 1971, 15, 109. (b) Aida, T. Prog. Polym. Sci. 1994, 19, 469. (c) Cheng, M.; Attygalle, A. B.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 11583. (d) Chamberlain, B. M.; Cheng, M.; Moore, D. R.; Ovitt, T. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 3229.
7.(a) Kim, S. H.; Han, Y. K.; Kim, Y. H.; Hong, S. I. Makromol. Chem. 1992, 193, 1623. (b) Sawhney, A.; Pathak, C. P.; Hubbell, J. A. Macromolecules 1993, 26, 581. (c) Zhang, X.; MacDonald, D. A.; Goosen, M. F. A.; McAuley, K. B. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 2965. (d) Han, D. K.; Hubbell, J. A. Macromolecules 1996, 29, 5233. (e) Kricheldorf, H. R.; Kreiser-Saunders: I.; Stricker, A. Macromolecules 2000, 33, 702.
8.(a) McLain, S. J.; Ford, T. M.; Drysdale, N. E. Polym. Prepr.(Am Chem. Soc., Div. Polym. Chem.) 1992, 33, 463. (b) Leborgne, A.; Pluta, C.; Spassky, N. Macromol. Rapid Commun. 1994, 15, 955. (c) Stevels, W. M.; Ankone, M. T.; Dijkstra, P. J.; Feijen, J. Macromolecules 1996, 29, 3332. (d) Li, S. M.; Rashkov, I.; Espartero, L.; Manolova, N.; Vert, M.
Macromolecules 1996, 29, 57.
9.(a) Jedlinski, Z.; Walach, W. Makromol. Chem. 1991, 192, 2051. (b) Chamberlain, B. M.; Sun, Y.; Hagadorn, J. R.; Hemmesch, E. W.; Young, V. G., Jr.; Pink, M.; Hillmyer, M. A.; Tolman, W. B. Macromolecules 1999, 32, 2400. (c) Simic, V.; Spassky, N.; Hubert-Pfalzgraf, I. G. Macromolecules 1997, 30, 7338. (d) Deng, X.; Yuan, M.; Xiong, C.; Li, X. J. Appl. Polym. Sci. 1999, 73, 1401.
10. Jerome, R.; Teyssie, P.; Vuillemin, B.; Zundel, T.; Zune, C. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 1-10 and references therein.
11. Lofgren, A.; Albertsson, A. C.; Dubois, P.; Jerome, R. J. Macromol. Sci. Rev. Macromol. Chem. Phys. 1995, C35, 379-418 and references therein.
12. Mulvey, R. E. Chem. Soc. Rev. 1998, 27, 339.
13. Save, M.; Schappacher, M.; Soum, A. Macromol. Chem. Phys. 2002, 203, 889.
14. Baran, J.; Duda, A.; Kowalski, A.; Szymanski, R.; Penczek, S. Macromol. Rapid Commun. 1997, 18, 325.
15. Ryner, M., Stridsberg, K., Albertsson, A. C., von Schenk, H., Svensson, M. Macromolecules 2001, 34, 3877.
16. (a) Yu, T. L.; Wu, C. C.; Chen, C. C.; Huang, B. H.; Wu, J. C.; Lin, C.C. Polymer 2005, 46, 5905.
References

1.(a) Thomas, E. L.; Anderson, D. M.; Henkee, C. S.; Hoffman, D. Nature 1988, 334, 598. (b) Matsen, M.W.; Bates, F. S. Macromolecules 1996, 29, 7641 and references therein.
2. (a) Schulz, M. F.; Bates, F. S.; Almdal, K.; Mortensen, K. Phys. Lett. 1994, 73, 86. (b) Hajduk, D. A.; Harper, P. E.; Gruner, S. M.; Honeker, C. C.; Kim, G.; Thomas, E. L.; Fetters, L. J. Macromolecules 1994, 27, 4063.
3. (a) Zalusky, A. S.; Olayo-Valles, R.; Taylor, C. J.; Hillmyer, M. A. J. Am. Chem. Soc. 2001, 123, 1519. (b) Zalusky, A. S.; Olayo-Valles, R.; Wolf, J. H.; Hillmyer, M. A. J. Am. Chem. Soc. 2002, 124, 12761. (c) Ho, R. M.; Chiang, Y. M.; Tsai, C. C.; Lin, C. C.; Ko, B. T.; Huang, B. H. J. Am. Chem. Soc. 2004, 126, 2704.
4. (a) Schmidt, S. C.; Hillmyer, M. A. Macromolecules 1999, 32, 4794. (b) Wang, Y.; Hillmyer, M. A. Macromolecules 2000, 33, 7395.
5. (a) Colombani, D. Prog. Polym. Sci. 1997, 22, 1649 and included references. (b)Controlled Radical Polymerization; Matyjaszewski, K. Ed.; ACS Symp. Ser. No. 685; American Chemical Society: Washington, DC, 1998 and included references.
6. (a) Solomon, D. H.; Rizzardo, E.; Cacioli, P. U.S. Patent 4581, March 27, 1985. (b) Rizzardo, E. Chem. Aust. 1987, 54,32. (c) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987. (d) Veregin, R. P. N.; Georges, M. K.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 5316. (e) Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185. (f) Moad, G.; Rizzardo, E. Macromolecules 1995, 28, 8722. (g) Kazmaier, P. M.; Moffat, K. A. Georges, M. K.; Veregin, R. P. N.; Hamer, G. K. Macromolecules 1995, 28, 1841. (h) Puts, R. D.; Sogah, D. Y. Macromolecules 1996, 29, 3323.
7.(a) Hawker, C. J.; Elce, E.; Dao, J.; Volksen, W.; Russell, T. P.; Barclay, G. G. Macromolecules 1996, 29, 2686. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987. (c) Zou, Y.; Lin, J.; Zhuang, R.; Ye, J.; Dai, L.; Zheng, L.; Macromolecules 2000, 33, 4745.
References
1.(a) Sapse, A. M. and Schleyer, P. v. R. (Eds.) Lithium Chemistry: A theoretical and Experimental Overview, John Wiley & Sons: New York, 1994 and (b) Schlosser, M. (Ed.) Orgonometallics in Synthesis-A Manual, 2 nd Edition, John Wiley & Sons: New York, 2002. (c) Rappoport, Z. and Marek, I. (Eds.) The Chemistry of Organolithium Compounds, John Wiley & Sons: New York, 2004. (d) Morton, M.; Wu, M. In Ring-Opening Polymerization: Kinetics, Mechanisms, and Synthesis; McGrath, J. E., Ed.; American Chemical Society: Washington, DC, 1985. (e) Boileau, S. In Anionic Polymerization: Kinetics, Mechanisms, and Synthesis; McGrath, J. E., Ed.; ACS Symposium Series 166, 1981; p 283. (f) Arnett, E. M.; Moe, K. D. J. Am. Chem. Soc. 1991, 113, 7068. (g) Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1183. (h) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624. (i) Ko, B. T.; Lin, C. C. J. Am. Chem. Soc. 2001, 123, 7973.
2.(a) Lochmann, L.; Pospisil, J.; Lim, D. Tetrahedron Lett. 1966, 257. (b) W. Bauer, L. Lochmann, J. Am. Chem. Soc. 1992, 114, 7482. (c) Schlosser, M. J. Organomet. Chem. 1967, 8, 9. (d) Lochmann, L Eur. J. Inorg. Chem. 2000, 6, 1115. (e) Lochmann, L.; Trekoval, J. J. Organomet. Chem. 1987, 326, 1. (f) Schlosser, M.; Strunk, S. Tetrahedron Lett. 1984, 25, 741. (g) Kennedy, A. R.; MacLellan, J. G.; Mulvey, R. E. Angew. Chem. Int. Ed. 2001, 40, 3245. (h) Wofford, C. F. US patent 3324191, 1966. (i) Hsieh, H. L.; Wofford, C. F. J. Polym. Sci. Polym. Chem. 1969, 7, 449.
3.(a) amide/enolate: Williard, P. G.; Hintze M. J. J. Am. Chem. Soc. 1987, 109, 5539; J. Am. Chem. Soc. 1990, 112, 8602. (b) enolate/alkoxide: Williard P. G.; MacEwan G. J. J. Am. Chem. Soc. 1989, 111, 7671. (c) alkyl/alkoxide: Marsch, M; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem. 1990, 29, 308. (d) Harder, S.; Streitwierser, A. Angew. Chem. 1993, 105, 1108. (e) turbo Grignard: Krasovskiy, A.; Knochel, P. Angew. Chem. Int. Ed. 2004, 43, 3336.; Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 2958.
4.(a) Nakamura, E.; Mori, S. Angew. Chem. Int. Ed. 2000, 39, 3750. (b) Nakamura, E.; Yamanaka, M. J. Am. Chem. Soc. 1999, 121, 8941. (c) Frantz, D. E.; Singleton, D. A. J. Am. Chem. Soc. 2000, 122, 3288. (d) Uchiyama, M.; Kameda, M.; Mishima, O.; Yokoyama, N.; Koike, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1998, 120, 4934. (e) Uchiyama, M.; Nakamura S.; Ohwada T.; Nakamura M.; Nakamura E. J. Am. Chem. Soc. 2004, 126, 10897. (f) Linton, D. J.; Schooler, P.; Wheatley, A. E. H. Coordination Chemistry Reviews 2001, 223, 53. (g) Nakamura, E.; Mori, S. Angew. Chem., Int. Ed. 2000, 39, 3750. (h) Oshima, K. J. Organomet. Chem. 1999, 575, 1.
5.(a) Kondo, Y.; Takazawa, N.; Yamazaki, C.; Sakamoto T. J. Org. Chem. 1994, 59, 4717. (b) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1996, 118, 8733. (c) Uchiyama, M.; Kameda, M.; Mishima, O.; Yokoyama, N.; Koike, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1998, 120, 4934. (d) Uchiyama, M.; Furumoto, S.; Saito, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc. 1997, 119, 11425. (e) Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539. (f) Uchiyama, M.; Miyoshi, T.; Kajihara, Y.; Sakamoto, T.; Otani, Y.; Ohwada, T.; Kondo, Y. J. Am. Chem. Soc. 2002, 124, 8514. (g) Imahori, T.; Uchiyama, M.; Sakamoto T.; Kondo, Y. Chem. Commun. 2001, 2450.
6.Uchiyama, M.; Matsumoto, Y.; Nakamura, S.; Ohwada, T.; Kobayashi, N.; Yamashita, N.; Matsumiya, A.; Sakamoto, T. J. Am. Chem. Soc. 2004, 126, 8755.
7.(a) Kitagawa, K.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem. Int. Ed. 2000, 39, 2481. (b) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333.
8.Hatano, M.; Matsumura, T.; Ishihara, K. Org. Lett., Vol. 7, No. 4, 2005, 573.
9.Richey, H. G.; Farkas, J. Organometallics 1990, 9, 1778.
10.(a) Baker, D. R.; Mulvey R. E. J. Am. Chem. Soc. 1993, 115, 6472. (b) Henderson, K. W.; Mulvey, R. E.; Friedrich, B. M. R. J. Am. Chem. Soc. 1994, 116, 10777. (c) Armstrong, D. R.; Clegg, W.; Drummond, A. M.; Liddle, S. T.; Mulvey R. E. J. Am. Chem. Soc. 2000, 122, 11117. (d) Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E.; Sherrington, D. C. Organometallics 2004, 23, 1197. (e) Nicholas D. R. B.; Clegg, W.; Kennedy, A. R.; Mulvey, R. E.; Weatherstonea, S. Chem. Commun. 2005, 375. (f) Andrikopoulos, P. C.; Armstrong, D. R.; Hevia, E.; Kennedy, A. R.; Mulvey R. E.; O’Hara, C. T. Chem. Commun. 2005, 1131. (g) Mulvey, R. E. Organometallics 2006, 25, 1060.
11.(a) Kennedy, A. R.; Mulvey, R. E.; Rowlings, R. B. J. Am. Chem. Soc. 1998, 120, 7816. (b) Kennedy, A. R.; Mulvey, R. E.; Rowlings, R. B. Angew. Chem. Int. Ed. 1998, 37, 1380. (c) Drummond, A. M.; Gibson, L. T.; Kennedy, A. R.; Mulvey, R. E.; O’Hara, C. T.; Rowlings, R. B.; Weightman, T. Angew. Chem. Int. Ed. 2002, 41, 2382. (d) Mulvey, R. E. Chem. Commun. 2001, 1049.
12.(a) Armstrong, D. R.; Kennedy, A. R.; Mulvey, R. E.; Rowlings R. B. Angew. Chem. Int. Ed. 1999, 38, 131. (b) Henderson, K. W.; Kennedy, A. R.; Mulvey, R. E.; O’Hara, C. T.; Rowlings, R. B. Chem. Commun. 2001, 1678. (c) Clegg, W.; Henderson, K. W.; Kennedy, A. R.; Mulvey, R. E.; O’Hara, C. T.; Rowlings, R. B.; Tooke, D. M. Angew. Chem. Int. Ed. 2001, 40, 3902. (d) Andrikopoulos, P. C.; Armstrong, D. R.; Clegg, W.; Gilfillan, C. J.; Hevia, E.; Kennedy, A. R.; Mulvey, R. E.; O’Hara, C. T.; Parkinson J. A.; Tooke, D. M. J. Am. Chem. Soc. 2004, 126, 11612. (e) Hevia, E.; Gallagher, D. J.; Kennedy, A. R.; Mulvey, R. E.; O’Hara, C. T.; Talmard, C. Chem. Commun. 2004, 2422. (f) Hevia, E.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E.; Sherrington, D. C. Angew. Chem. Int. Ed. 2005, 44, 68. (g) Andrikopoulos, P. C.; Armstrong, D. R.; Graham, D. V.; Hevia, E. Kennedy, A. R.; Mulvey, R. E.; O’Hara, C. T.; Talmard, C. Angew. Chem. Int. Ed. 2005, 44, 3459. (h) Andrikopoulos, P. C.; Armstrong, D. R.; Barley, H. R. L.; Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E. J. Am. Chem. Soc. 2005, 127, 6184. (i) Barley, H. R. L.; Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E. Angew. Chem. Int. Ed. 2005, 44, 6018. (j) Graham, D. V.; Hevia, E.; Kennedy, A. R.; Mulvey, R. E.; O’Hara, C. T.; Talmard, C. Chem. Commun. 2006, 417.
13.(a) He, X.; Noll, B. C.; Beatty, A.; Mulvey, R. E.; Henderson, K. W. J. Am. Chem. Soc. 2004, 126, 7444. (b) Hevia, E.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E. J. Am. Chem. Soc. 2005, 127, 13106. (c) Hevia, E.; Henderson, K. W.; Kennedy, A. R.; Mulvey, R. E. Organometallics 2006, 25,1778.
14.(a) Ménoret, S.; Fontanille, M.; Deffieux, A. Macromolecules 2002, 35, 4584. (b) Ménoret, S.; Deffieux, A.; Desbois, P. Macromolecules 2003, 36, 5988. (c) Hsieh, H. L.; Wang, I. W. Macromolecules 1986, 19, 299. (d) Zolotareva, I. V.; Arest-Yakubovich, A. A. Macromolecules 1999, 32, 4141.
15.Maréchal, J. M.; Carlotti, S.; Shcheglova, L.; Deffieux, A. Polymer 2004, 45, 4641.
16.Mulvey, R. E. Chem. Soc. Rev. 1998, 27, 339.
17.(a) Harrowfield, J. M.; Ogden, M. I.; Richmond, W. R.; White, A. H. Chem. Commun. 1991, 1159. (b) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303. (c) Meadows, E. S.; de Wall, S. L.; Barbour, L. J.; Gokel, G. W. J. Am. Chem. Soc. 2001, 123, 3092. (d) Hu, J.; Barbour, L. J.; Ferdani, R.; Gokel, G. W. Chem. Commun. 2002, 1806. (e) Gokel, G. W.; Barbour, L. J.; Ferdani, R.; Hu, J. Acc. Chem. Res. 2002, 35, 878. (f) Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210. (g) Cametti, M.; Nissinen, M.; Cort, A. D.; Mandolini, L.; Rissanen, K. J. Am. Chem. Soc. 2005, 127, 3831. (h) Åhman, A.; Nissinen, M. Chem. Commun. 2006, 1209.
18.(a) Bolig, A. D.; Chen, E. Y. X. J. Am. Chem. Soc. 2001, 123, 7943. (b) Cui, C.; Shafir, A.; Reeder, C. L.; Arnold, J. Organometallics 2003, 22, 3357. (c) Dove, A. P.; Gibson, V. C.; Marshall, E. L.; White, A. J. P.; Williams, D. J. Chem. Commun. 2002, 1208.
19.Rodriguez-Delgado, A.; Mariott, W. R.; Chen, E. Y. X. Macromolecules 2004, 37, 3092. (b) Bolig, A. D.; Chen, E. Y. X. J. Am. Chem. Soc. 2004, 126, 4897.
20.(a) Goode, W. E.; Owens, F. H.; Myers, W. L. Crystalline acrylic polymers. II. Mechanism studies. J Polym Sci 1960, 47, 75. (b) Goode, W. E.; Owens, F. H.; Fellwann, R. P.; Snyder, W. H. Moore, J. E. Crystalline acrylic polymers. I. Stereospecific anionic polymerization of methylmethacrylate. J Polym Sci 1960, 46, 317. (c) Glusker, D. L.; Stiles, E.; Yonkoskie, B. J Polym Sci 1961, 49, 297.
Reference
1. Allen, R. D.; Long, T. E.; McGrath, J. E. Polym. Bull. 1986, 15, 127.
連結至畢業學校之論文網頁點我開啟連結
註: 此連結為研究生畢業學校所提供,不一定有電子全文可供下載,若連結有誤,請點選上方之〝勘誤回報〞功能,我們會盡快修正,謝謝!
QRCODE
 
 
 
 
 
                                                                                                                                                                                                                                                                                                                                                                                                               
第一頁 上一頁 下一頁 最後一頁 top
無相關期刊