메뉴 건너뛰기




Volumn 121, Issue 2, 1999, Pages 326-334

Secondary deuterium kinetic isotope effects in irreversible additions of hydride and carbon nucleophiles to aldehydes: A spectrum of transition states from complete bond formation to single electron transfer

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DEUTERIUM; LITHIUM DERIVATIVE;

EID: 0033585616     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982504r     Document Type: Article
Times cited : (43)

References (64)
  • 1
    • 0003417469 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vols. 1 and 2.
    • (1991) Comprehensive Organic Synthesis , vol.1-2
  • 2
    • 0003942864 scopus 로고
    • John Wiley & Sons: New York
    • Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 875-888. Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418 (for calculations with A1H3). Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem., Int. Ed. Engl. 1992, 31, 1019 (for caculations with LiH).
    • (1994) Stereochemistry of Organic Compounds , pp. 875-888
    • Eliel, E.L.1    Wilen, S.H.2    Mander, L.N.3
  • 3
    • 33751154573 scopus 로고
    • Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 875-888. Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418 (for calculations with A1H3). Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem., Int. Ed. Engl. 1992, 31, 1019 (for caculations with LiH).
    • (1995) J. Org. Chem. , vol.60 , pp. 418
    • Coxon, J.M.1    Houk, K.N.2    Luibrand, R.T.3
  • 4
    • 33748232180 scopus 로고
    • Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 875-888. Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418 (for calculations with A1H3). Wu, Y.-D.; Houk, K. N.; Paddon-Row, M. N. Angew. Chem., Int. Ed. Engl. 1992, 31, 1019 (for caculations with LiH).
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 1019
    • Wu, Y.-D.1    Houk, K.N.2    Paddon-Row, M.N.3
  • 5
    • 0000410844 scopus 로고
    • For a review with a penetrating analysis, see: Walling, C. J. Am. Chem. Soc. 1988, 110, 6846.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6846
    • Walling, C.1
  • 7
    • 0040668486 scopus 로고
    • (a) Yamataka, H.; Hanafusa, T. J. Org. Chem. 1988, 53, 772. All reactions had a small positive ρ value, except for reaction with 9BBN, which had a negative p value.
    • (1988) J. Org. Chem. , vol.53 , pp. 772
    • Yamataka, H.1    Hanafusa, T.2
  • 8
    • 33845376058 scopus 로고
    • (b) Yamataka, H.; Hanafusa, T. J. Am. Chem. Soc. 1986, 108, 6643. (NaBH4 in IPA and LiBH4 in ether, 1.066 and 1.089, respectively; LAH in ether, 1.024.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6643
    • Yamataka, H.1    Hanafusa, T.2
  • 9
    • 0001250846 scopus 로고
    • Ashby, E. C.; Bowers, J. R., Jr. J. Am. Chem. Soc. 1981, 103, 2242. See also: Ashby, E. C.; Chao, L.-C.; Neumann, H. M.; Laemmle, J. T. Acc. Chem. Res. 1974, 7, 272. Ashby, E. C. Pure Appl. Chem. 1980, 52, 545; Acc. Chem. Res. 1988, 21, 414. Holm, T. Acta Chem. Scand. 1983, B37, 569.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 2242
    • Ashby, E.C.1    Bowers J.R., Jr.2
  • 10
    • 0001284174 scopus 로고
    • Ashby, E. C.; Bowers, J. R., Jr. J. Am. Chem. Soc. 1981, 103, 2242. See also: Ashby, E. C.; Chao, L.-C.; Neumann, H. M.; Laemmle, J. T. Acc. Chem. Res. 1974, 7, 272. Ashby, E. C. Pure Appl. Chem. 1980, 52, 545; Acc. Chem. Res. 1988, 21, 414. Holm, T. Acta Chem. Scand. 1983, B37, 569.
    • (1974) Acc. Chem. Res. , vol.7 , pp. 272
    • Ashby, E.C.1    Chao, L.-C.2    Neumann, H.M.3    Laemmle, J.T.4
  • 11
    • 0000374154 scopus 로고
    • Ashby, E. C.; Bowers, J. R., Jr. J. Am. Chem. Soc. 1981, 103, 2242. See also: Ashby, E. C.; Chao, L.-C.; Neumann, H. M.; Laemmle, J. T. Acc. Chem. Res. 1974, 7, 272. Ashby, E. C. Pure Appl. Chem. 1980, 52, 545; Acc. Chem. Res. 1988, 21, 414. Holm, T. Acta Chem. Scand. 1983, B37, 569.
    • (1980) Pure Appl. Chem. , vol.52 , pp. 545
    • Ashby, E.C.1
  • 12
    • 33845280639 scopus 로고
    • Ashby, E. C.; Bowers, J. R., Jr. J. Am. Chem. Soc. 1981, 103, 2242. See also: Ashby, E. C.; Chao, L.-C.; Neumann, H. M.; Laemmle, J. T. Acc. Chem. Res. 1974, 7, 272. Ashby, E. C. Pure Appl. Chem. 1980, 52, 545; Acc. Chem. Res. 1988, 21, 414. Holm, T. Acta Chem. Scand. 1983, B37, 569.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 414
  • 13
    • 0001250846 scopus 로고
    • Ashby, E. C.; Bowers, J. R., Jr. J. Am. Chem. Soc. 1981, 103, 2242. See also: Ashby, E. C.; Chao, L.-C.; Neumann, H. M.; Laemmle, J. T. Acc. Chem. Res. 1974, 7, 272. Ashby, E. C. Pure Appl. Chem. 1980, 52, 545; Acc. Chem. Res. 1988, 21, 414. Holm, T. Acta Chem. Scand. 1983, B37, 569.
    • (1983) Acta Chem. Scand. , vol.B37 , pp. 569
    • Holm, T.1
  • 18
    • 0030689011 scopus 로고    scopus 로고
    • Yamataka, H.; Sasaki, D.; Kuwantani, Y.; Mishima, M.; Tsuno, Y. Chem. Lett. 1997, 271; J. Am. Chem. Soc. 1997, 119, 9975.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9975
  • 19
    • 0040074832 scopus 로고
    • do Amaral, L.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1972, 94, 7579. do Amaral, L.; Bastos, M. P.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1973, 95, 7369. Archila, J.; Bull, H. G.; Lagenaur, C. J. Org. Chem. 1971, 36, 1345. Pires, J. R.; Stachissini, A. S.; do Amaral, L. J. Phys. Org. Chem. 1994, 7, 192. Rossi, M. H.; Stachissini, A. S.; do Amaral, L. J. Org. Chem. 1990, 55, 1300.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 7579
    • Do Amaral, L.1    Bull, H.G.2    Cordes, E.H.3
  • 20
    • 0007689601 scopus 로고
    • do Amaral, L.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1972, 94, 7579. do Amaral, L.; Bastos, M. P.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1973, 95, 7369. Archila, J.; Bull, H. G.; Lagenaur, C. J. Org. Chem. 1971, 36, 1345. Pires, J. R.; Stachissini, A. S.; do Amaral, L. J. Phys. Org. Chem. 1994, 7, 192. Rossi, M. H.; Stachissini, A. S.; do Amaral, L. J. Org. Chem. 1990, 55, 1300.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 7369
    • Do Amaral, L.1    Bastos, M.P.2    Bull, H.G.3    Cordes, E.H.4
  • 21
    • 0038890435 scopus 로고
    • do Amaral, L.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1972, 94, 7579. do Amaral, L.; Bastos, M. P.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1973, 95, 7369. Archila, J.; Bull, H. G.; Lagenaur, C. J. Org. Chem. 1971, 36, 1345. Pires, J. R.; Stachissini, A. S.; do Amaral, L. J. Phys. Org. Chem. 1994, 7, 192. Rossi, M. H.; Stachissini, A. S.; do Amaral, L. J. Org. Chem. 1990, 55, 1300.
    • (1971) J. Org. Chem. , vol.36 , pp. 1345
    • Archila, J.1    Bull, H.G.2    Lagenaur, C.3
  • 22
    • 84985493588 scopus 로고
    • do Amaral, L.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1972, 94, 7579. do Amaral, L.; Bastos, M. P.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1973, 95, 7369. Archila, J.; Bull, H. G.; Lagenaur, C. J. Org. Chem. 1971, 36, 1345. Pires, J. R.; Stachissini, A. S.; do Amaral, L. J. Phys. Org. Chem. 1994, 7, 192. Rossi, M. H.; Stachissini, A. S.; do Amaral, L. J. Org. Chem. 1990, 55, 1300.
    • (1994) J. Phys. Org. Chem. , vol.7 , pp. 192
    • Pires, J.R.1    Stachissini, A.S.2    Do Amaral, L.3
  • 23
    • 0025274331 scopus 로고
    • do Amaral, L.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1972, 94, 7579. do Amaral, L.; Bastos, M. P.; Bull, H. G.; Cordes, E. H. J. Am. Chem. Soc. 1973, 95, 7369. Archila, J.; Bull, H. G.; Lagenaur, C. J. Org. Chem. 1971, 36, 1345. Pires, J. R.; Stachissini, A. S.; do Amaral, L. J. Phys. Org. Chem. 1994, 7, 192. Rossi, M. H.; Stachissini, A. S.; do Amaral, L. J. Org. Chem. 1990, 55, 1300.
    • (1990) J. Org. Chem. , vol.55 , pp. 1300
    • Rossi, M.H.1    Stachissini, A.S.2    Do Amaral, L.3
  • 25
    • 0000724623 scopus 로고    scopus 로고
    • (b) Others (Abu-Hasanayn, F.; Streitwieser, A. J. Org. Chem. 1998, 63, 2954) found a large inverse equilibrium SDIE in the addition of a lithium enolate to benzaldehyde.
    • (1998) J. Org. Chem. , vol.63 , pp. 2954
    • Abu-Hasanayn, F.1    Streitwieser, A.2
  • 26
    • 0011575560 scopus 로고
    • 13C isotope effects in this work are controversial, but the deuterium effects are reproduced by theory: Hrovat, D. A.; Hammonds, J. H.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523. Thus, to the extent that an olefinic sp2 carbon becomes a radical-like carbon in the radical anion, the frequencies at that carbon should be lower, see also: Pacansky, J.; Koch, W.; Miller, M. D. J. Am. Chem. Soc. 1991, 113, 317.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 532
    • Stevenson, G.R.1    Espe, M.P.2    Reiter, R.C.3
  • 27
    • 0030728866 scopus 로고    scopus 로고
    • 13C isotope effects in this work are controversial, but the deuterium effects are reproduced by theory: Hrovat, D. A.; Hammonds, J. H.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523. Thus, to the extent that an olefinic sp2 carbon becomes a radical-like carbon in the radical anion, the frequencies at that carbon should be lower, see also: Pacansky, J.; Koch, W.; Miller, M. D. J. Am. Chem. Soc. 1991, 113, 317.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9523
    • Hrovat, D.A.1    Hammonds, J.H.2    Stevenson, C.D.3    Borden, W.T.4
  • 28
    • 0001384724 scopus 로고
    • 13C isotope effects in this work are controversial, but the deuterium effects are reproduced by theory: Hrovat, D. A.; Hammonds, J. H.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523. Thus, to the extent that an olefinic sp2 carbon becomes a radical-like carbon in the radical anion, the frequencies at that carbon should be lower, see also: Pacansky, J.; Koch, W.; Miller, M. D. J. Am. Chem. Soc. 1991, 113, 317.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 317
    • Pacansky, J.1    Koch, W.2    Miller, M.D.3
  • 29
    • 0344176752 scopus 로고    scopus 로고
    • note
    • (a) The calculated value for the equilibrium: acetaldehyde-H + conjugate acid-D ⇌ acetaldehyde-D + conjugate acid-H is 0.83 at 25 °C at the MP2/6-31G** level with no scaling of frequencies.
  • 30
    • 33847800139 scopus 로고
    • (b) Jencks, W. P. Acc. Chem. Res. 1976, 9, 425-32. Funderburk, L. H.; Aldwin, L.; Jencks, W. P. J. Am. Chem. Soc. 1978, 100, 5444-59. Hill, E. A.; Milosevich, S. A. Tetrahedron Lett. 1976, 4553-54. The possibility that both protonation and nucleophilic attack are reversible with the rate-determining step involving general base catalysis in the removal of a proton, which would also give rise to general acid catalysis, is not involved.
    • (1976) Acc. Chem. Res. , vol.9 , pp. 425-432
    • Jencks, W.P.1
  • 31
    • 33947094308 scopus 로고
    • (b) Jencks, W. P. Acc. Chem. Res. 1976, 9, 425-32. Funderburk, L. H.; Aldwin, L.; Jencks, W. P. J. Am. Chem. Soc. 1978, 100, 5444-59. Hill, E. A.; Milosevich, S. A. Tetrahedron Lett. 1976, 4553-54. The possibility that both protonation and nucleophilic attack are reversible with the rate-determining step involving general base catalysis in the removal of a proton, which would also give rise to general acid catalysis, is not involved.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 5444-5459
    • Funderburk, L.H.1    Aldwin, L.2    Jencks, W.P.3
  • 32
    • 0009498804 scopus 로고
    • (b) Jencks, W. P. Acc. Chem. Res. 1976, 9, 425-32. Funderburk, L. H.; Aldwin, L.; Jencks, W. P. J. Am. Chem. Soc. 1978, 100, 5444-59. Hill, E. A.; Milosevich, S. A. Tetrahedron Lett. 1976, 4553-54. The possibility that both protonation and nucleophilic attack are reversible with the rate-determining step involving general base catalysis in the removal of a proton, which would also give rise to general acid catalysis, is not involved.
    • (1976) Tetrahedron Lett. , pp. 4553-4554
    • Hill, E.A.1    Milosevich, S.A.2
  • 33
    • 3343019305 scopus 로고
    • Shiner, V. J., Jr.; Neumann, T. E. Z. Naturforsch. 1989, 44a, 337. For earlier work on fractionation factors, see: Hartshorn, S. R.; Shiner, V. J., Jr. J. Am. Chem. Soc. 1972, 91, 9002.
    • (1989) Z. Naturforsch. , vol.44 A , pp. 337
    • Shiner V.J., Jr.1    Neumann, T.E.2
  • 34
    • 0000486650 scopus 로고
    • Shiner, V. J., Jr.; Neumann, T. E. Z. Naturforsch. 1989, 44a, 337. For earlier work on fractionation factors, see: Hartshorn, S. R.; Shiner, V. J., Jr. J. Am. Chem. Soc. 1972, 91, 9002.
    • (1972) J. Am. Chem. Soc. , vol.91 , pp. 9002
    • Hartshorn, S.R.1    Shiner V.J., Jr.2
  • 35
    • 4143127677 scopus 로고
    • For a systematic theoretical study of small-molecule deuterium fractionation factors, see: Harris, N. J. J. Phys. Chem. 1995, 99, 14689.
    • (1995) J. Phys. Chem. , vol.99 , pp. 14689
    • Harris, N.J.1
  • 37
    • 0000467538 scopus 로고
    • (b) For an excellent review, see: Wigfield, D. C. Tetrahedron 1979, 35, 449.
    • (1979) Tetrahedron , vol.35 , pp. 449
    • Wigfield, D.C.1
  • 39
    • 33847089228 scopus 로고
    • DeFrees, D. J.; Bartmess, J. E.; Kim, J. K.; McIver, R. T., Jr.; Hehre, W. J. J. Am. Chem. Soc. 1977, 99, 6451. These authors showed that the equilibration of methanol and trideuteriomethoxide with trideuteriomethanol and methoxide favored the latter pair by 0.5 kcal/mol at room temperature in an ICR cell.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 6451
    • DeFrees, D.J.1    Bartmess, J.E.2    Kim, J.K.3    McIver R.T., Jr.4    Hehre, W.J.5
  • 43
    • 0000009978 scopus 로고
    • (c) Eliel, E. L.; Senda, Y. Tetrahedron 1970, 26, 2411. Ashby, E. C.; Boone, J. R. J. Am. Chem. Soc. 1976. 98, 5524.
    • (1970) Tetrahedron , vol.26 , pp. 2411
    • Eliel, E.L.1    Senda, Y.2
  • 51
    • 0009268728 scopus 로고
    • Carbonyl Compounds
    • Bard, A. J., Lund, H., Eds.; Marcel Dekker: New York
    • Evans, D. H. Carbonyl Compounds. In Encyclopedia of Electrochemistry of the Elements, Vol XII; Bard, A. J., Lund, H., Eds.; Marcel Dekker: New York, 1978; pp 1-259.
    • (1978) Encyclopedia of Electrochemistry of the Elements , vol.12 , pp. 1-259
    • Evans, D.H.1
  • 52
    • 0000289680 scopus 로고
    • Palmer, C. A.; Ogle, C. A.; Arnett, E. M. J. Am. Chem. Soc. 1992, 114, 5619. This paper provides an excellent review of the efforts to distinguish between rate-determining C-C bond formation and SET.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5619
    • Palmer, C.A.1    Ogle, C.A.2    Arnett, E.M.3
  • 54
    • 0000085002 scopus 로고
    • Arnett, E. M.; Moe, K. J. Am. Chem. Soc. 1991, 113, 7068. See also: Arnett, E. M.; Palmer, C. A. J. Am. Chem. Soc. 1990, 112, 7354.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7068
    • Arnett, E.M.1    Moe, K.2
  • 55
    • 0001340527 scopus 로고
    • Arnett, E. M.; Moe, K. J. Am. Chem. Soc. 1991, 113, 7068. See also: Arnett, E. M.; Palmer, C. A. J. Am. Chem. Soc. 1990, 112, 7354.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7354
    • Arnett, E.M.1    Palmer, C.A.2
  • 56
    • 0004183235 scopus 로고
    • John Wiley & Sons: New York
    • From Benson's Group Additivity Tables: Benson, S. W. Thermochemical Kinetics, 2nd ed.; John Wiley & Sons: New York, 1976; pp 272-275.
    • (1976) Thermochemical Kinetics, 2nd Ed. , pp. 272-275
    • Benson, S.W.1
  • 62
    • 36849137629 scopus 로고
    • Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261. Wolfsberg, M. Acc. Chem. Res. 1972, 5, 225. Hout, R. F., Jr.; Wolfsberg, M.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 3296.
    • (1947) J. Chem. Phys. , vol.15 , pp. 261
    • Bigeleisen, J.1    Mayer, M.G.2
  • 63
    • 0000032005 scopus 로고
    • Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261. Wolfsberg, M. Acc. Chem. Res. 1972, 5, 225. Hout, R. F., Jr.; Wolfsberg, M.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 3296.
    • (1972) Acc. Chem. Res. , vol.5 , pp. 225
    • Wolfsberg, M.1
  • 64
    • 0009464648 scopus 로고
    • Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261. Wolfsberg, M. Acc. Chem. Res. 1972, 5, 225. Hout, R. F., Jr.; Wolfsberg, M.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 3296.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 3296
    • Hout R.F., Jr.1    Wolfsberg, M.2    Hehre, W.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.