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Volumn 121, Issue 48, 1999, Pages 11237-11238

An unusual isotope effect in the reactions of the naphthylcarbenes [8]

Author keywords

[No Author keywords available]

Indexed keywords

ISOTOPE; NAPHTHALENE DERIVATIVE;

EID: 0033537023     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9917013     Document Type: Letter
Times cited : (6)

References (35)
  • 4
    • 0001938664 scopus 로고
    • For reviews of the chemistry of atomic carbon, see: (a) Skell, P. S.; Havel, J. J.; McGlinchey, M. J. Acc. Chem. Res. 1973, 6, 97. (b) MacKay, C. In Carbenes; Moss, R. A., Jones, M., Jr., Eds.; Wiley-Interscience: New York, 1975; Vol. II, pp 1-42. (c) Shevlin, P. B. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1980; Vol. I, pp 1-36.
    • (1973) Acc. Chem. Res. , vol.6 , pp. 97
    • Skell, P.S.1    Havel, J.J.2    McGlinchey, M.J.3
  • 5
    • 0003128343 scopus 로고
    • Moss, R. A., Jones, M., Jr., Eds.; Wiley-Interscience: New York
    • For reviews of the chemistry of atomic carbon, see: (a) Skell, P. S.; Havel, J. J.; McGlinchey, M. J. Acc. Chem. Res. 1973, 6, 97. (b) MacKay, C. In Carbenes; Moss, R. A., Jones, M., Jr., Eds.; Wiley-Interscience: New York, 1975; Vol. II, pp 1-42. (c) Shevlin, P. B. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1980; Vol. I, pp 1-36.
    • (1975) Carbenes , vol.2 , pp. 1-42
    • MacKay, C.1
  • 6
    • 0002627789 scopus 로고
    • Abramovitch, R. A., Ed.; Plenum Press: New York
    • For reviews of the chemistry of atomic carbon, see: (a) Skell, P. S.; Havel, J. J.; McGlinchey, M. J. Acc. Chem. Res. 1973, 6, 97. (b) MacKay, C. In Carbenes; Moss, R. A., Jones, M., Jr., Eds.; Wiley-Interscience: New York, 1975; Vol. II, pp 1-42. (c) Shevlin, P. B. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1980; Vol. I, pp 1-36.
    • (1980) Reactive Intermediates , vol.1 , pp. 1-36
    • Shevlin, P.B.1
  • 7
    • 84920351433 scopus 로고    scopus 로고
    • note
    • The experimental setup is described in ref 1. Carbon atoms and substrate were co-condensed at 77 K, and products were anaylzed by GC, GC/MS, and NMR.
  • 14
    • 84920362068 scopus 로고    scopus 로고
    • note
    • 11
  • 16
    • 0001424728 scopus 로고
    • Deoxygenation of aryl aldehydes is known to generate chemically activated carbenes: Rahman, M.; Shevlin, P. B. Tetrahedron Lett. 1985, 26, 2959.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2959
    • Rahman, M.1    Shevlin, P.B.2
  • 18
    • 36849137629 scopus 로고
    • D > 1 for the rearrangement of 1 to 4 was calculated using the method of Bigeleisen and Mayer: Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261. The calculations used the program QUIVER (Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989).
    • (1947) J. Chem. Phys. , vol.15 , pp. 261
    • Bigeleisen, J.1    Mayer, M.G.2
  • 19
    • 0024841752 scopus 로고
    • D > 1 for the rearrangement of 1 to 4 was calculated using the method of Bigeleisen and Mayer: Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261. The calculations used the program QUIVER (Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989).
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8989
    • Saunders, M.1    Laidig, K.E.2    Wolfsberg, M.3
  • 20
    • 84920354803 scopus 로고    scopus 로고
    • note
    • D for this step would be small.
  • 22
    • 84920341590 scopus 로고    scopus 로고
    • note
    • 8 compounds in the GC/MS.
  • 23
    • 84920342137 scopus 로고    scopus 로고
    • note
    • 8 on THF yields 4:(5 + 6) = 3.70), isotope effects in the presence and absence of 2-butene cannot be directly compared.
  • 24
    • 84920360388 scopus 로고    scopus 로고
    • note
    • 2. Increasing this pressure increases the ratio of (7 + 8):(5 + 6).
  • 25
  • 26
    • 0000749982 scopus 로고
    • Birks, J. B., Ed.; John Wiley & Sons: New York
    • (b) Henry, B. R.; Siebrand, W. In Organic Molecular Photophysics; Birks, J. B., Ed.; John Wiley & Sons: New York, 1973; Vol. 1, pp 153-237.
    • (1973) Organic Molecular Photophysics , vol.1 , pp. 153-237
    • Henry, B.R.1    Siebrand, W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.