Bulletin of the Korean Chemical Society

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Kinetic Topochemical Effect on Methanol Insertion into Phenyl-α-ketocarbene

  • Sung, Dae Dong (Department of Chemistry, Dong-A University) ;
  • Ryu, Zoon Ha (Department of Chemistry, Dong-Eui University) ;
  • Jeong, Min-Ho (Department of Microbiology, Medical School, Dong-A University) ;
  • Kim, Yong-Ho (College of Biomedical Science and Engineering, Inje University) ;
  • Lee, Ik-Choon (Department of Chemistry, Inha University) ;
  • Bilehal, Dinesh, C. (Department of Chemistry, Dong-A University)
  • Published : 2008.12.20
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References

  1. Stubb, S. I.; Braun, P. V. Science in Molecular Manipulation of Microstructures: Biomaterials, Ceramics, and Semiconductors; 1997; Vol. 277(#5330), pp 1242-1248
  2. Tomioka, H.; Izawa, Y. J. Am. Chem. Soc. 1977, 99, 6128 https://doi.org/10.1021/ja00460a062
  3. Platz, M. S. Kinetics and Spectroscopy of Carbene and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; p 165
  4. Barcus, R. L.; Hadel, C. M.; Johnston, L. J.; Paltz, M. S.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1986, 108, 3928 https://doi.org/10.1021/ja00274a013
  5. Hadel, L. M.; Maloney, V. M.; Platz, M. S.; McGimpsey, W. F.; Scaiano, J. C. J. Phys. Chem. 1986, 90, 2488 https://doi.org/10.1021/j100402a044
  6. Griller, D.; Hadel, L. M.; Nazram, A. S.; Platz, M. S.; Wong, P. C.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 2227 https://doi.org/10.1021/ja00320a001
  7. Tomioka, H. J. Am. Chem. Soc. 1979, 101, 256 https://doi.org/10.1021/ja00495a062
  8. Schmidt, G. M. J. In Solid State Photochemistry; Ginsberg, D., Ed.; Verlag-Chemie: Weinheim, 1976; p 2
  9. Scheffer, J. R. Acc. Chem. Res. 1980, 13, 283 https://doi.org/10.1021/ar50152a006
  10. Moss, R. A.; Dolling, U.-H. J. Am. Chem. Soc. 1971, 93, 954 https://doi.org/10.1021/ja00733a029
  11. Moss, R. A.; Huselton, J. K. J. Am. Chem. Soc. 1978, 100, 1314 https://doi.org/10.1021/ja00472a059
  12. Likhotvorik, I.; Zhu, Z.; Tae, E. L.; Tippmann, E.; Hill, B. T.; Platz, M. S. J. Am. Chem. Soc. 2001, 123, 6061 https://doi.org/10.1021/ja004235m
  13. Admasu, A.; Platz, M. S.; Marcinek, A.; Michalak, J.; Gudmundsdüttir, A. D.; Gebicki, A. J. J. Phys. Org. Chem. 1997, 10, 207 https://doi.org/10.1002/(SICI)1099-1395(199704)10:4<207::AID-POC883>3.0.CO;2-8
  14. Moss, R. A.; Joyce, M. A. J. Am. Chem. Soc. 1978, 100, 4475 https://doi.org/10.1021/ja00482a027
  15. Moss, R. A.; Shen, S.; Hadel, L. M.; Kmiecik, L. G.; Wostowska, J.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1987, 109, 4341 https://doi.org/10.1021/ja00248a034
  16. Moore, J. A.; Reed, D. E. Org. Synth. Collec. 1973; Vol. V, p 351
  17. Peachy, N. M.; Eckhardt, C. J. J. Am. Chem. Soc. 1993, 115, 3519 https://doi.org/10.1021/ja00062a016
  18. Enyo, T.; Arai, N.; Nakane, N.; Nicolaides, A.; Tomioka, H. J. Org. Chem. 2005, 70, 7744 https://doi.org/10.1021/jo0512204
  19. Savino, T. G.; Kanakarajan, K.; Platz, M. S. J. Org. Chem. 1986, 51, 1305 https://doi.org/10.1021/jo00358a027
  20. Sung, D. D.; Kang, D. Y.; Ryu, Z. H. Bull. Korean Chem. Soc. 1997, 18(9), 945
  21. Sung, D. D.; Choi, M. J.; Ha, K. M.; Um, T. S. Bull. Korean Chem. Soc. 1999, 20(8), 935
  22. Sung, D. D.; Lee, J. P.; Lee, Y. H.; Ryu, Z. H.; Ryu, W. S. J. Photosci. 2000, 7(1), 15
  23. Sung, D. D.; Jeung, J. H.; Ryu, Z. H.; Chin, W. B.; Lee, I. Bull. Korean Chem. Soc. 2004, 25(8), 1231 https://doi.org/10.5012/bkcs.2004.25.8.1231
  24. Wang, J.-L.; Yuzawa, T.; Nigam, M.; Likhotvorik, I.; Platz, M. S. J. Phys. Chem. A 2001, 105, 3752 https://doi.org/10.1021/jp001726k
  25. Kirmse, W. Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 1-57
  26. Fujiwara, Y.; Tanimoto, Y.; Itoh, M.; Hirai, K.; Tomioka, H. J. Am. Chem. Soc. 1987, 109, 1942 https://doi.org/10.1021/ja00241a008
  27. Kirms, W.; Kilian, J.; Steenken, S. J. Am. Chem. Soc. 1990, 112, 6399 https://doi.org/10.1021/ja00173a039
  28. Moss, R. A.; Zheng, F.; Fedé, J.-M.; Ma, Y.; Sauers, R. R.; Toscano, J. P.; Showalte, B. M. J. Am. Chem. Soc. 2002, 124, 5258 https://doi.org/10.1021/ja020002e
  29. Wang, Y.; Hadad, C. M.; Toscano, J. P. J. Am. Chem. Soc. 2002, 124, 1761 https://doi.org/10.1021/ja012139v
  30. Dix, E. J.; Herman, M. S.; Goodman, J. L. J. Am. Chem. Soc. 1993, 115, 10424 https://doi.org/10.1021/ja00075a094
  31. Kawano, M.; Hirai, K.; Tomioka, H.; Ohashi, Y. J. Am. Chem. Soc. 2007, 129, 2383 https://doi.org/10.1021/ja067306b
  32. Wierlacher, S.; Sander, W.; Liu, M. T. J. Am. Chem. Soc. 1993, 115, 8943 https://doi.org/10.1021/ja00073a008
  33. Chan, H. S.; Dill, K. A. Proteins: Structure, Function, and Genetics 30; 1998; pp 2-33 https://doi.org/10.1002/(SICI)1097-0134(19980101)30:1<2::AID-PROT2>3.0.CO;2-R
  34. Matagne, A.; Jamin, M.; Chung, E. W.; Robinson, C. V.; Radford, S. E.; Dobson, C. M. J. Mol. Biol. 2000, 297, 193 https://doi.org/10.1006/jmbi.2000.3540
  35. Silva, C. R.; Li, J.; Zheng, Z.; Corrales, R. J. Phys. Chem. A 2008, 112, 4527 https://doi.org/10.1021/jp8002799
  36. Fichthorn, K.; Balan, P. G. J. Chem. Phys. 1994, 101, 10028 https://doi.org/10.1063/1.467991
  37. Krok, F.; Abrahams, I.; Kario, A.; Malys, M.; Dygas, J. R. Solid State Ionics 2008, 179, 172 https://doi.org/10.1016/j.ssi.2007.12.028
  38. Stavola, M.; Cheng, Y. M. Solid Stae Commun. 1995, 93, 431 https://doi.org/10.1016/0038-1098(94)00812-4
  39. Miller, R.; Danko, C. A.; Fasolka, J.; Balazs, A. C.; Chan, H. S.; Dill, K. A. J. Chem. Phys. 1992, 96, 768 https://doi.org/10.1063/1.462462
  40. Tomioka, H.; Ueda, H.; Kondo, S.; Izawa, Y. J. Am. Chem. Soc. 1980, 102, 7817 https://doi.org/10.1021/ja00546a049
  41. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: New York, 1980
  42. Caldin, E. F. Chem. Rev. 1969, 69, 135 https://doi.org/10.1021/cr60257a006
  43. Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; p 203
  44. Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. S.; Jones, Jr. M., Eds.; Wiley-Interscience: New Jersey, 2004; pp 375- 461
  45. Gilbert, B. C.; Griller, D.; Nazran, A. S. J. Org. Chem. 1985, 50, 4738 https://doi.org/10.1021/jo00224a016
  46. Alt, R.; Gould, I. R.; Staab, H. A.; Turro, N. J. J. Am. Chem. Soc. 1986, 108, 6911 https://doi.org/10.1021/ja00282a013
  47. Sugiyama, M. H.; Celebi, S.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 966 https://doi.org/10.1021/ja00029a027
  48. Wasserman, E.; Trozzolo, A. M.; Yager, W. A. J. Chem. Phys. 1964, 40, 2408
  49. Trozzolo, A. M.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1965, 87, 129 https://doi.org/10.1021/ja01079a030
  50. Lapin, S. C.; Brauer, B.-E.; Schuster, G. W. J. Am. Chem. Soc. 1984, 106, 2092 https://doi.org/10.1021/ja00319a032
  51. Lapin, S. C.; Schuster, G. B. J. Am. Chem. Soc. 1985, 107, 4243 https://doi.org/10.1021/ja00300a028
  52. Sitzman, E. V.; Eisenthal, K. B. In Applications of Picosecond Spectroscopy to Chemistry; Reidel Publishing: Dordrecht, The Netherlands, 1983; pp 41-63
  53. Grass, P. B.; Brauer, B.-E.; Zupancic, J. J.; Kaufman, K. J.; Schuster, G. B. J. Am. Chem. Soc. 1983, 105, 6833 https://doi.org/10.1021/ja00361a014
  54. Humphreys, R. W. R.; Arnold, D. R. Can. J. Chem. 1979, 57, 2652 https://doi.org/10.1139/v79-430
  55. Arnold, D. R.; Humphreys, W. R. J. Chem. Soc., Chem. Commun. 1978, 181
  56. Geise, C. M.; Hadad, C. M. J. Org. Chem. 2000, 65, 8348 https://doi.org/10.1021/jo005655x
  57. Geise, C. M.; Hadad, C. M. J. Am. Chem. Soc. 2002, 124, 355 https://doi.org/10.1021/ja012079t