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Volumn 121, Issue 49, 1999, Pages 11478-11485

Theoretical studies of the additions of germylenes to ethylene

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; ETHYLENE; GERMANIUM DERIVATIVE;

EID: 0033573030     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990954t     Document Type: Article
Times cited : (46)

References (63)
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    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1971) Carbene Chemistry, 2nd Ed.
    • Kirmse, W.1
  • 3
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    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1973) Carbenes , vol.1
    • Moss, R.A.1    Jones M., Jr.2
  • 4
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    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1975) Carbenes , vol.2
    • Jones M., Jr.1    Moss, R.A.2
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    • (1978) Reactive Intermediates , pp. 1
    • Moss, R.A.1    Jones M., Jr.2
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    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1981) Reactive Intermediates , vol.2
    • Moss, R.A.1    Jones M., Jr.2
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    • Wiley: New York
    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1985) Reactive Intermediates , vol.3
    • Moss, R.A.1    Jones M., Jr.2
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    • 0004035157 scopus 로고
    • Plenum: New York
    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1980) Reactive Intermediates , vol.1
    • Abramovitch, R.A.1
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    • Plenum: New York
    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1990) Kinetics and Spectroscopy of Carbenes and Biradicals
    • Platz, M.S.1
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    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1980) Acc. Chem. Res. , vol.13 , pp. 58
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    • and references therein
    • For reviews and pertinent references see: (a) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971. (b) Moss, R. A.; Jones, M., Jr. Carbenes; Wiley: New York. 1973; Vol. 1. (c) Jones, M., Jr.; Moss, R. A. Carbenes; Wiley: New York, 1975; Vol. 2. (d) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1978; Vol. 1. (e) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1981; Vol. 2. (f) Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3. (g) Abramovitch, R. A. Reactive Intermediates; Plenum: New York, 1980; Vol. 1. (h) Platz, M. S. Kinetics And Spectroscopy of Carbenes And Biradicals; Plenum: New York, 1990. (i) Moss, R. A. Acc. Chem. Res. 1980, 13, 58. (j) Moss, R. A. Acc. Chem. Res. 1989, 22, 15 and references therein.
    • (1989) Acc. Chem. Res. , vol.22 , pp. 15
    • Moss, R.A.1
  • 12
    • 0342716204 scopus 로고    scopus 로고
    • note
    • Although there is a substantially larger number of examples in which careful work gives results in accord with the Skell-Woodworth hypothesis, there are several examples of failure in the stereochemistry of carbene addition. In fact, the Skell-Woodworth hypothesis should be regarded as reasonable intuition rather than sound theory since there is no firm basis for the presumption that rotation about single bonds will necessarily be much more rapid than spin inversion. Indeed, it has been proved that spin inversion plays a central role in triplet carbene cycloaddition. For details see ref 4.
  • 52
    • 0342281193 scopus 로고    scopus 로고
    • note
    • Nevertheless, in this respect the theoretical studies of Houk et al. are of interest. Using an ab initio technique these workers have found that for certain systems, interaction of carbene and alkene is sufficiently strong so that there is no enthalpic barrier to product formation, and that no potential energy minimum exists for a complex. For details see ref 17.
  • 57
    • 0342281169 scopus 로고    scopus 로고
    • Manuscript in preparation
    • Su, M.-D.; Chu, S.-Y. Manuscript in preparation.
    • Su, M.-D.1    Chu, S.-Y.2
  • 62
    • 0343150666 scopus 로고    scopus 로고
    • note
    • 2 = 0.926.
  • 63
    • 0342281165 scopus 로고    scopus 로고
    • note
    • 2 = 0.891.


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