Studies of ring-opening reactions of styrene oxide by chromium tetraphenylporphyrin initiators. Mechanistic and stereochemical considerations

Macromolecules

Volumn 46, Issue 3, 2013, Pages 692-698

  Harrold, Nicole D ^a   Li, Yang ^a   Chisholm, Malcolm H ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL HPLC; CHROMIUM(III); COORDINATION CATALYSIS; IMINIUM; METHINE; NUCLEOPHILIC ATTACK; ORGANIC CHEMISTRY; POLY(STYRENE OXIDE); RING OPENING; RING OPENING REACTION; STYRENE CARBONATES; STYRENE OXIDE; TETRAPHENYL PORPHYRINS; TRIPHENYL PHOSPHINES;

CATALYSIS; CHLORINE COMPOUNDS; CHROMIUM; LEAD OXIDE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

STYRENE;

EID: 84873681636     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma302492p     Document Type: Article

References (32)

1. Ishii, Y.; Sakai, S. 1,2-Epoxides. In Ring-Opening Polymerization; Frisch, K. C., Reegen, S. L., Eds.; Marcel Dekker: New York, 1969.
2. Inoue, S.; Aida, T. Cyclic Ethers. In Ring-Opening Polymerization; Ivin, K. J., Saegusa, T., Eds.; Elsevier: New York, 1984; Vol. 1.
3. Szwarc, M.; Van Beylen, M. Ionic Polymerization and Living Polymers; Chapman & Hall: New York, 1993.
4. Slomkowski, S.; Duda, A. Anionic Ring-Opening Polymerization. In Ring-Opening Polymerization. Mechanism, Catalysis, Structure, Utility; Brunelle, D. J., Ed.; Hanser: Munich, 1993.
5. Sugimoto, H.; Inoue, S. Adv. Polym. Sci. 1999, 146, 39
6. Inoue, S. J. Polym. Sci., Polym. Chem. Ed. 2000, 38, 2861
7. Sugimoto, H.; Kawamura, C.; Kuroki, M.; Aida, T.; Inoue, S. Macromolecules 1994, 27, 2013
8. Hill, F. N.; Bailey, F. E.; Fitzpatrick, J. T. Ind. Eng. Chem. 1958, 50, 5
9. Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897
10. Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924
11. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421
12. Darensbourg, D. J. Chem. Rev. 2007, 107, 2388
13. Coates, G. W.; Moore, D. R. Angew. Chem., Int. Ed. 2004, 43, 6618
14. Darensbourg, D. J.; Mackiewicz, R. M.; Phelps, A. L.; Billodeaux, D. R. Acc. Chem. Res. 2004, 37, 836
15. Chisholm, M. H.; Zhou, Z. J. Mater. Chem. 2004, 14, 3081
16. Sugimoto, H.; Inoue, S. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 5561
17. Kember, M. R.; Buchard, A.; Williams, C. K. Chem. Commun 2010, not supplied.
18. Darensbourg, D. J.; Yarbrough, J. C. J. Am. Chem. Soc. 2002, 124, 6335
19. Chisholm, M. H.; Zhou, Z. J. Am. Chem. Soc. 2003, 126, 11030
20. Wu, G.-P.; Wei, S.-H.; Lu, X.-B.; Ren, W.-M.; Darensbourg, D. J. Macromolecules 2010, 43, 9202
21. Wu, G.-P.; Wei, S.-H.; Ren, W.-M.; Lu, X.-B.; Li, B.; Zu, Y.-P.; Darensbourg, D. J. Energy Environ. Sci. 2011, 4, 5084
22. Lu, X.-B.; Darensbourg, D. J. Chem. Soc. Rev. 2012, 41, 1462
23. Lin, B.; Whalen, D. L. J. Org. Chem. 1994, 59, 1638
24. Antelmann, B.; Chisholm, M. H.; Iyer, S. S.; Huffman, J. C.; Navarro-Llobet, D.; Pagel, M. Macromolecules 2001, 34, 3159
25. Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39
26. DePuy, C. H.; Breitbeil, F. W.; DeBruin, K. R. J. Am. Chem. Soc. 1966, 88, 3347
27. Chatterjee, C. A Comparative Study of Porphyrin Metal (III) Catalysts with Al, Co, or Cr Centers for the Synthesis of Polyethers, Polycarbonates, and Polyesters. PhD, The Ohio State University, Columbus, OH, 2012.
28. Jeske, R. C.; DiCiccio, A. M.; Coates, G. W. J. Am. Chem. Soc. 2007, 129, 11330
29. Nejad, E. H.; Paoniasari, A.; Koning, C. E.; Duchateau, R. Polym. Chem. 2012, 3, 1308
30. Darensbourg, D. J.; Poland, R. R.; Escobedo, C. Macromolecules 2012, 45, 2242
31. Ren, W.-M.; Wu, G.-P.; Lin, F.; Jiang, J.-Y.; Liu, C.; Luo, Y.; Lu, X.-B. Chem. Sci. 2012, 3, 2094
32. Lu, X.-B.; Ren, W.-M.; Wu, G.-P. Acc. Chem. Res. 2012, 45, 1721