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Volumn 44, Issue 3, 1999, Pages 439-443

Hydrogen transfer from catalyst intermediate prototypes to stabilized radicals

Author keywords

Absolute rates; Benzyl radical; Free radicals; Hydrogen transfer; Kinetics; Organometallic hydrides

Indexed keywords


EID: 0039778388     PISSN: 05693772     EISSN: None     Source Type: Conference Proceeding    
DOI: None     Document Type: Article
Times cited : (3)

References (31)
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    • (a) Curran, D. P. Synthesis 1988, 6, 417-39, (b) Baguley, P. A.; Walton, J. C. Angew. Chem. Int. Ed. 1998, 37, 3072-3082, (c) Davies, A. G. Organotin Chemistry; WILEY-VCH: Weinheim, 1997.
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    • Baguley, P.A.1    Walton, J.C.2
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    • WILEY-VCH: Weinheim
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    • Organotin Chemistry , pp. 1997
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    • For examples, see (a) Bakac, A. Inorg. Chem. 1998, 37, 3548-3552, (b) Ash, E. A.; Hurd, P. W.; Darensbourg, M. Y.; Newcomb, M. J. J. Am. Chem. Soc. 1987, 109, 3313-3317, (c) Bullock, R. M.; Samsel, E. G. J. Am. Chem. Soc. 1990, 112, 6886-6898, (d) Eisenberg, D. C.; Lawrie, C. J. C.; Moody, A. E.; Norton, J. R. J. Am. Chem. Soc. 1991, 113, 4888-4895, (e) Eisenberg, D. C.; Norton, J. R. Isr. J. Chem. 1991, 31, 55-66, (f) Kinney, R. J.; Jones, W. D.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902-7915.
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    • 0001193406 scopus 로고
    • For examples, see (a) Bakac, A. Inorg. Chem. 1998, 37, 3548-3552, (b) Ash, E. A.; Hurd, P. W.; Darensbourg, M. Y.; Newcomb, M. J. J. Am. Chem. Soc. 1987, 109, 3313-3317, (c) Bullock, R. M.; Samsel, E. G. J. Am. Chem. Soc. 1990, 112, 6886-6898, (d) Eisenberg, D. C.; Lawrie, C. J. C.; Moody, A. E.; Norton, J. R. J. Am. Chem. Soc. 1991, 113, 4888-4895, (e) Eisenberg, D. C.; Norton, J. R. Isr. J. Chem. 1991, 31, 55-66, (f) Kinney, R. J.; Jones, W. D.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902-7915.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4888-4895
    • Eisenberg, D.C.1    Lawrie, C.J.C.2    Moody, A.E.3    Norton, J.R.4
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    • 85005746639 scopus 로고
    • For examples, see (a) Bakac, A. Inorg. Chem. 1998, 37, 3548-3552, (b) Ash, E. A.; Hurd, P. W.; Darensbourg, M. Y.; Newcomb, M. J. J. Am. Chem. Soc. 1987, 109, 3313-3317, (c) Bullock, R. M.; Samsel, E. G. J. Am. Chem. Soc. 1990, 112, 6886-6898, (d) Eisenberg, D. C.; Lawrie, C. J. C.; Moody, A. E.; Norton, J. R. J. Am. Chem. Soc. 1991, 113, 4888-4895, (e) Eisenberg, D. C.; Norton, J. R. Isr. J. Chem. 1991, 31, 55-66, (f) Kinney, R. J.; Jones, W. D.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902-7915.
    • (1991) Isr. J. Chem. , vol.31 , pp. 55-66
    • Eisenberg, D.C.1    Norton, J.R.2
  • 11
    • 0001417979 scopus 로고
    • For examples, see (a) Bakac, A. Inorg. Chem. 1998, 37, 3548-3552, (b) Ash, E. A.; Hurd, P. W.; Darensbourg, M. Y.; Newcomb, M. J. J. Am. Chem. Soc. 1987, 109, 3313-3317, (c) Bullock, R. M.; Samsel, E. G. J. Am. Chem. Soc. 1990, 112, 6886-6898, (d) Eisenberg, D. C.; Lawrie, C. J. C.; Moody, A. E.; Norton, J. R. J. Am. Chem. Soc. 1991, 113, 4888-4895, (e) Eisenberg, D. C.; Norton, J. R. Isr. J. Chem. 1991, 31, 55-66, (f) Kinney, R. J.; Jones, W. D.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902-7915.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 7902-7915
    • Kinney, R.J.1    Jones, W.D.2    Bergman, R.G.3
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    • 0000721252 scopus 로고
    • See, e.g. (a) Alnajjar, M.S. and Franz, J.A. J. Am. Chem. Soc. 1992, 114, 1052, (b) Autrey, S.T.; Alnajjar, M.S.; Nelson, D.A.; and Franz, J.A. J. Org. Chem 1991, 56, 2197.
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    • Alnajjar, M.S.1    Franz, J.A.2
  • 14
    • 0001180629 scopus 로고
    • (a) Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200-266, (b) Lehni, M.; Schuh, H.; Fischer, H. Int. J. Chem. Kinet. 1979, 11, 705-713. (c) Claridge, R. F. C.; Fischer, H. J. Phys. Chem. 1983, 87, 1960-1967, (d) Huggenberger, C.; Fischer, H. Helv. Chim. Acta 1981, 64, 338-353.
    • (1987) Acc. Chem. Res. , vol.20 , pp. 200-266
    • Fischer, H.1    Paul, H.2
  • 15
    • 84985393647 scopus 로고
    • (a) Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200-266, (b) Lehni, M.; Schuh, H.; Fischer, H. Int. J. Chem. Kinet. 1979, 11, 705-713. (c) Claridge, R. F. C.; Fischer, H. J. Phys. Chem. 1983, 87, 1960-1967, (d) Huggenberger, C.; Fischer, H. Helv. Chim. Acta 1981, 64, 338-353.
    • (1979) Int. J. Chem. Kinet. , vol.11 , pp. 705-713
    • Lehni, M.1    Schuh, H.2    Fischer, H.3
  • 16
    • 0000278239 scopus 로고
    • (a) Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200-266, (b) Lehni, M.; Schuh, H.; Fischer, H. Int. J. Chem. Kinet. 1979, 11, 705-713. (c) Claridge, R. F. C.; Fischer, H. J. Phys. Chem. 1983, 87, 1960-1967, (d) Huggenberger, C.; Fischer, H. Helv. Chim. Acta 1981, 64, 338-353.
    • (1983) J. Phys. Chem. , vol.87 , pp. 1960-1967
    • Claridge, R.F.C.1    Fischer, H.2
  • 17
    • 84985160168 scopus 로고
    • (a) Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200-266, (b) Lehni, M.; Schuh, H.; Fischer, H. Int. J. Chem. Kinet. 1979, 11, 705-713. (c) Claridge, R. F. C.; Fischer, H. J. Phys. Chem. 1983, 87, 1960-1967, (d) Huggenberger, C.; Fischer, H. Helv. Chim. Acta 1981, 64, 338-353.
    • (1981) Helv. Chim. Acta , vol.64 , pp. 338-353
    • Huggenberger, C.1    Fischer, H.2
  • 18
    • 0041181444 scopus 로고    scopus 로고
    • note
    • See ref. 5b for a detailed description of the procedure for obtaining von Smoluchowski rate expressions.
  • 20
    • 0039994196 scopus 로고    scopus 로고
    • Polarizable radicals may not be well served by this assumption, but benzyl radical is well-behaved: (a) Okamoto, K.; Hirota, N.; and Terazima, M. J. Chem. Soc. Far. Trans. 1998, 94(2), 185 and J. Phys. Chem. A. 1997, 101, 5269.
    • (1998) Chem. Soc. Far. Trans. , vol.94 , Issue.2 , pp. 185
    • Okamoto, K.1    Hirota, N.2    Terazima, M.J.3
  • 21
    • 0031189668 scopus 로고    scopus 로고
    • Polarizable radicals may not be well served by this assumption, but benzyl radical is well-behaved: (a) Okamoto, K.; Hirota, N.; and Terazima, M. J. Chem. Soc. Far. Trans. 1998, 94(2), 185 and J. Phys. Chem. A. 1997, 101, 5269.
    • (1997) J. Phys. Chem. A. , vol.101 , pp. 5269
  • 22
    • 0001975107 scopus 로고
    • Compounds 1 and 2: (a) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1975, 88, C21. (b) Shaply, J.R., Keister, J.B.; Churchill, M.R., J. Am. Chem. Soc., 1975, 97, 4145. (c) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1976, 114, 313. Compounds 4,5, and 6: Kabir, S.E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Cresswell, W.; Gringstaff, J., Organometallics, 1995, 14, 3611. Arcia, E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Ciurash, J.; Duque, R.; Osella, D.; Gogetto, R.; Milone, L., Organometallics, 1998, 17, 415 . Compound 3: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 54-5 6 Compound 7: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 48-50. Compounds 8 and 10 purchased from Strem Chemicals.
    • (1975) J. Organomet. Chem. , vol.88
    • Deeming, A.J.1    Hasso, S.J.2
  • 23
    • 33847802366 scopus 로고
    • Compounds 1 and 2: (a) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1975, 88, C21. (b) Shaply, J.R., Keister, J.B.; Churchill, M.R., J. Am. Chem. Soc., 1975, 97, 4145. (c) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1976, 114, 313. Compounds 4,5, and 6: Kabir, S.E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Cresswell, W.; Gringstaff, J., Organometallics, 1995, 14, 3611. Arcia, E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Ciurash, J.; Duque, R.; Osella, D.; Gogetto, R.; Milone, L., Organometallics, 1998, 17, 415 . Compound 3: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 54-5 6 Compound 7: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 48-50. Compounds 8 and 10 purchased from Strem Chemicals.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 4145
    • Shaply, J.R.1    Keister, J.B.2    Churchill, M.R.3
  • 24
    • 0000513449 scopus 로고
    • Compounds 1 and 2: (a) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1975, 88, C21. (b) Shaply, J.R., Keister, J.B.; Churchill, M.R., J. Am. Chem. Soc., 1975, 97, 4145. (c) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1976, 114, 313. Compounds 4,5, and 6: Kabir, S.E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Cresswell, W.; Gringstaff, J., Organometallics, 1995, 14, 3611. Arcia, E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Ciurash, J.; Duque, R.; Osella, D.; Gogetto, R.; Milone, L., Organometallics, 1998, 17, 415 . Compound 3: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 54-5 6 Compound 7: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 48-50. Compounds 8 and 10 purchased from Strem Chemicals.
    • (1976) J. Organomet. Chem. , vol.114 , pp. 313
    • Deeming, A.J.1    Hasso, S.J.2
  • 25
    • 0007280517 scopus 로고
    • Compounds 1 and 2: (a) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1975, 88, C21. (b) Shaply, J.R., Keister, J.B.; Churchill, M.R., J. Am. Chem. Soc., 1975, 97, 4145. (c) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1976, 114, 313. Compounds 4,5, and 6: Kabir, S.E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Cresswell, W.; Gringstaff, J., Organometallics, 1995, 14, 3611. Arcia, E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Ciurash, J.; Duque, R.; Osella, D.; Gogetto, R.; Milone, L., Organometallics, 1998, 17, 415 . Compound 3: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 54-5 6 Compound 7: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 48-50. Compounds 8 and 10 purchased from Strem Chemicals.
    • (1995) Organometallics , vol.14 , pp. 3611
    • Kabir, S.E.1    Kolwaite, D.S.2    Rosenberg, E.3    Hardcastle, K.4    Cresswell, W.5    Gringstaff, J.6
  • 26
    • 11744303115 scopus 로고    scopus 로고
    • Compounds 1 and 2: (a) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1975, 88, C21. (b) Shaply, J.R., Keister, J.B.; Churchill, M.R., J. Am. Chem. Soc., 1975, 97, 4145. (c) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1976, 114, 313. Compounds 4,5, and 6: Kabir, S.E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Cresswell, W.; Gringstaff, J., Organometallics, 1995, 14, 3611. Arcia, E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Ciurash, J.; Duque, R.; Osella, D.; Gogetto, R.; Milone, L., Organometallics, 1998, 17, 415 . Compound 3: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 54-5 6 Compound 7: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 48-50. Compounds 8 and 10 purchased from Strem Chemicals.
    • (1998) Organometallics , vol.17 , pp. 415
    • Arcia, E.1    Kolwaite, D.S.2    Rosenberg, E.3    Hardcastle, K.4    Ciurash, J.5    Duque, R.6    Osella, D.7    Gogetto, R.8    Milone, L.9
  • 27
    • 0037572671 scopus 로고
    • Compounds 1 and 2: (a) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1975, 88, C21. (b) Shaply, J.R., Keister, J.B.; Churchill, M.R., J. Am. Chem. Soc., 1975, 97, 4145. (c) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1976, 114, 313. Compounds 4,5, and 6: Kabir, S.E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Cresswell, W.; Gringstaff, J., Organometallics, 1995, 14, 3611. Arcia, E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Ciurash, J.; Duque, R.; Osella, D.; Gogetto, R.; Milone, L., Organometallics, 1998, 17, 415 . Compound 3: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 54-5 6 Compound 7: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 48-50. Compounds 8 and 10 purchased from Strem Chemicals.
    • (1974) Inorganic Synthesis , vol.15 , pp. 54-56
    • Ahmad, N.1    Levison, J.J.2    Robenson, S.D.3    Uttley, M.F.4    Parshall, G.W.5
  • 28
    • 0003038887 scopus 로고
    • Compounds 1 and 2: (a) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1975, 88, C21. (b) Shaply, J.R., Keister, J.B.; Churchill, M.R., J. Am. Chem. Soc., 1975, 97, 4145. (c) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1976, 114, 313. Compounds 4,5, and 6: Kabir, S.E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Cresswell, W.; Gringstaff, J., Organometallics, 1995, 14, 3611. Arcia, E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Ciurash, J.; Duque, R.; Osella, D.; Gogetto, R.; Milone, L., Organometallics, 1998, 17, 415 . Compound 3: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 54-5 6 Compound 7: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 48-50. Compounds 8 and 10 purchased from Strem Chemicals.
    • (1974) Inorganic Synthesis , vol.15 , pp. 48-50
    • Ahmad, N.1    Levison, J.J.2    Robenson, S.D.3    Uttley, M.F.4    Parshall, G.W.5
  • 29
    • 0039402204 scopus 로고    scopus 로고
    • note
    • Compounds 1 and 2: (a) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1975, 88, C21. (b) Shaply, J.R., Keister, J.B.; Churchill, M.R., J. Am. Chem. Soc., 1975, 97, 4145. (c) Deeming, A.J.; Hasso, S. J., J. Organomet. Chem., 1976, 114, 313. Compounds 4,5, and 6: Kabir, S.E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Cresswell, W.; Gringstaff, J., Organometallics, 1995, 14, 3611. Arcia, E.; Kolwaite, D.S.; Rosenberg, E.; Hardcastle, K.; Ciurash, J.; Duque, R.; Osella, D.; Gogetto, R.; Milone, L., Organometallics, 1998, 17, 415 . Compound 3: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 54-5 6 Compound 7: Ahmad, N.; Levison, J. J., Robenson, S. D.; Uttley, M. F.; Parshall, G. W. ed., Inorganic Synthesis, 1974, 15, 48-50. Compounds 8 and 10 purchased from Strem Chemicals.


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