Tandem ring-opening/ring-closing metathesis polymerization: Relationship between monomer structure and reactivity

Journal of the American Chemical Society

Volumn 135, Issue 29, 2013, Pages 10769-10775

  Park, Hyeon ^a   Lee, Ho Keun ^a   Choi, Tae Lim ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTION; END-GROUP ANALYSIS; METATHESIS POLYMERIZATION; POLYMER REPEAT UNITS; POLYMERIZATION OF MONOMERS; POLYMERIZATION RATES; STRUCTURAL MODIFICATIONS; STRUCTURE-REACTIVITY RELATIONSHIPS;

FUNCTIONAL GROUPS; LIVING POLYMERIZATION; OLEFINS; POLYMERS; REACTION RATES;

MONOMERS;

ALKYNE; ALKYNE DERIVATIVE; CYCLOALKENE; CYCLOHEXENE DERIVATIVE; MONOMER;

ARTICLE; CHEMICAL STRUCTURE; DIELS ALDER REACTION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STRUCTURE ACTIVITY RELATION; TANDEM RING OPENING METATHESIS POLYMERIZATION;

EID: 84880795956     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4039278     Document Type: Article

References (63)

1. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413
2. Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013
3. Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Weinheim, 2003; Vols. 1, 2.
4. Grubbs, R. H. Tetrahedron 2004, 60, 7117
5. Novak, B. M.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 960
6. Schrock, R. R. Acc. Chem. Res. 1990, 23, 158
7. Bielawski, C. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2000, 39, 2903
8. Wagener, K. B.; Boncella, J. M.; Nel, J. G. Macromolecules 1991, 24, 2649
9. Patton, J. T.; Boncella, J. M.; Wagener, K. B. Macromolecules 1992, 25, 3862
10. Brzezinska, K.; Wolfe, P. S.; Watson, M. D.; Wagener, K. B. Macromol. Chem. Phys. 1996, 197, 2065
11. Mutlu, H.; Montero de Espinosa, L.; Meier, M. A. R. Chem. Soc. Rev. 2011, 40, 1404
12. Choi, S.-K.; Gal, Y.-S.; Jin, S.-H.; Kim, H. K. Chem. Rev. 2000, 100, 1645
13. Fox, H. H.; Wolf, M. O.; Odell, R.; Lin, B. L.; Schrock, R. R.; Wrington, M. S. J. Am. Chem. Soc. 1994, 116, 2827
14. Anders, U.; Nuyken, O.; Buchmeiser, M. R.; Wurst, K. Angew. Chem., Int. Ed. 2002, 41, 4044
15. Anders, U.; Nuyken, O.; Buchmeiser, M. R.; Wurst, K. Macromolecules 2002, 35, 9029
16. Mayershofer, M. G.; Nuyken, O.; Buchmeiser, M. R. Macromolecules 2006, 39, 3484
17. Kang, E.-H.; Lee, I. S.; Choi, T.-L. J. Am. Chem. Soc. 2011, 133, 11904
18. Kim, J.; Kang, E.-H.; Choi, T.-L. ACS Macro Lett. 2012, 1, 1090
19. Kang, E.-H.; Lee, I.-H.; Choi, T.-L. ACS Macro Lett. 2012, 1, 1098
20. Lee, I. S.; Kang, E.-H.; Choi, T.-L. Chem. Sci. 2012, 3, 761
21. Irvin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997.
22. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417
23. Song, A.; Parker, K. A.; Sampson, N. S. J. Am. Chem. Soc. 2009, 131, 3444
24. Song, A.; Parker, K. A.; Sampson, N. S. Org. Lett. 2010, 12, 3203
25. Katsumata, T.; Shiotsuki, M.; Kuroki, S.; Ando, I.; Masuda, T. Polym. J. 2005, 37, 608
26. Katsumata, T.; Shiotsuki, M.; Masuda, T. Macromol. Chem. Phys. 2006, 207, 1244
27. Csabai, P.; Joó, F.; Trzeciak, A. M.; Ziółkowski, J. J. J. Organomet. Chem. 2006, 691, 3371
28. Katsumata, T.; Shiotsuki, M.; Sanda, F.; Sauvage, X.; Delaude, L.; Masuda, T. Macromol. Chem. Phys. 2009, 210, 1891
29. Wallace, K. C.; Liu, A. H.; Davis, W. M.; Schrock, R. R. Organometallics 1989, 8, 644
30. Schrock, R. R.; Luo, S.; Zanetti, N. C.; Fox, H. H. Organometallics 1994, 13, 3396
31. Buchmeiser, M.; Schrock, R. R. Macromolecules 1995, 28, 6642
32. Kim, H.-S.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801
33. Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291
34. Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417
35. Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648
36. Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2002, 43, 7469
37. Maifeld, S. A.; Miller, R. L.; Lee, D. J. Am. Chem. Soc. 2004, 126, 12228
38. Park, H.; Hong, Y.-L.; Kim, Y.; Choi, T.-L. Org. Lett. 2010, 12, 3442
39. Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356
40. Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287
41. Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773
42. Virolleaud, M.-A.; Bressy, C.; Piva, O. Tetrahedron Lett. 2003, 44, 8081
43. Boyer, F.-D.; Hanna, I.; Ricard, L. Org. Lett. 2004, 6, 1817
44. Quinn, K. J.; Isaacs, A. K.; Arvary, R. A. Org. Lett. 2004, 6, 4143
45. Niethe, A.; Fischer, D.; Blechert, S. J. Org. Chem. 2008, 73, 3088
46. Cros, F.; Pelotier, B.; Piva, O. Eur. J. Org. Chem. 2010, 5063
47. Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161
48. Ruckert, A.; Eisele, D.; Blechert, S. Tetrahedron Lett. 2001, 42, 5245
49. Randl, S.; Lucas, N.; Connon, S. J.; Blechert, S. Adv. Synth. Catal. 2002, 344, 631
50. Mori, M.; Kuzuba, Y.; Kitamura, T.; Sato, Y. Org. Lett. 2002, 4, 3855
51. Bantl, D.; North, M. Adv. Synth. Catal. 2002, 344, 694
52. For a review on tandem enyne metathesis reactions, see: Li, J.; Lee, D. Eur. J. Org. Chem. 2011, 4269
53. Royer, F.; Vilain, C.; Elkaïm, L.; Grimaud, L. Org. Lett. 2003, 5, 2007
54. Cho, J.; Lee, Y. M.; Kim, D.; Kim, S. J. Org. Chem. 2009, 74, 3900
55. Kotha, S.; Waghule, G. T. J. Org. Chem. 2012, 77, 6314
56. Fustero, S.; Bello, P.; Miró, J.; Simón, A.; del Pozo, C. Chem.-Eur. J. 2012, 18, 10991
57. Park, H.; Choi, T.-L. J. Am. Chem. Soc. 2012, 134, 7270
58. Heji, A.; Scherman, O. A.; Grubbs, R. H. Macromolecules 2005, 38, 7214
59. Lee, I. S.; Kang, E.-H.; Park, H.; Choi, T.-L. Chem. Sci. 2012, 3, 761
60. Batzer, H.; Reblin, H. Makromol. Chem. 1961, 179, 44
61. Bell, V. L. J. Polym. Sci., Part A: Polym. Chem. 1964, 2, 5305
62. Gramlich, W. M.; Hillmyer, M. A. Polym. Chem. 2011, 2, 2062
63. Lee, S. J.; McGinnis, J.; Katz, T. J. J. Am. Chem, Soc. 1976, 98, 7818