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Volumn 119, Issue 52, 1997, Pages 12772-12778

Electrophilic addition to η2-aldehyde complexes of pentaammineosmium(II): The formation of Fischer carbyne complexes via η2- aldehydium intermediates

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; OSMIUM;

EID: 0031593064     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972766d     Document Type: Article
Times cited : (20)

References (44)
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    • For reviews of the Fischer-Tropsch reaction, see (a) Wender, I. Fuel Processing Technol. 1996, 48, 189. (b) Herrmann, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, 1996; Vol 2, Chapter 3.1.8. (c) Muetterties, E. L.; Stein, J. Chem. Rev. 1979, 79, 479.
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  • 2
    • 0030231594 scopus 로고    scopus 로고
    • Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, Chapter 3.1.8
    • For reviews of the Fischer-Tropsch reaction, see (a) Wender, I. Fuel Processing Technol. 1996, 48, 189. (b) Herrmann, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, 1996; Vol 2, Chapter 3.1.8. (c) Muetterties, E. L.; Stein, J. Chem. Rev. 1979, 79, 479.
    • (1996) Applied Homogeneous Catalysis with Organometallic Compounds , vol.2
    • Herrmann, W.A.1
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    • For reviews of the Fischer-Tropsch reaction, see (a) Wender, I. Fuel Processing Technol. 1996, 48, 189. (b) Herrmann, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, 1996; Vol 2, Chapter 3.1.8. (c) Muetterties, E. L.; Stein, J. Chem. Rev. 1979, 79, 479.
    • (1979) Chem. Rev. , vol.79 , pp. 479
    • Muetterties, E.L.1    Stein, J.2
  • 4
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    • For reviews of transition metal aldehyde complexes, see: (a) Delbecq, F.; Sautet, P. J. Am. Chem. Soc. 1992, 114, 2446. (b) Huang, Y.-H.; Gladysz, J. A. J. Chem. Ed. 1988, 60, 298.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2446
    • Delbecq, F.1    Sautet, P.2
  • 5
    • 0000424358 scopus 로고
    • For reviews of transition metal aldehyde complexes, see: (a) Delbecq, F.; Sautet, P. J. Am. Chem. Soc. 1992, 114, 2446. (b) Huang, Y.-H.; Gladysz, J. A. J. Chem. Ed. 1988, 60, 298.
    • (1988) J. Chem. Ed. , vol.60 , pp. 298
    • Huang, Y.-H.1    Gladysz, J.A.2
  • 15
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    • 2-pentaammine-osmium(II) complexes, see: (a) Kolis, S. P.; Gonzalez, J.; Bright, L. M.; Harman, W. D. Organometallics 1996, 15, 245. (b) Spera, M. L.; Harman, W. D. Organometallics 1995, 14, 1559. (c) Hodges, L. M.; Gonzalez, J.; Koontz, J. I.; Myers, W. H.; Harman, W. D. J. Org. Chem. 1995, 60, 2125.
    • (1996) Organometallics , vol.15 , pp. 245
    • Kolis, S.P.1    Gonzalez, J.2    Bright, L.M.3    Harman, W.D.4
  • 16
    • 0000460350 scopus 로고
    • 2-pentaammine-osmium(II) complexes, see: (a) Kolis, S. P.; Gonzalez, J.; Bright, L. M.; Harman, W. D. Organometallics 1996, 15, 245. (b) Spera, M. L.; Harman, W. D. Organometallics 1995, 14, 1559. (c) Hodges, L. M.; Gonzalez, J.; Koontz, J. I.; Myers, W. H.; Harman, W. D. J. Org. Chem. 1995, 60, 2125.
    • (1995) Organometallics , vol.14 , pp. 1559
    • Spera, M.L.1    Harman, W.D.2
  • 17
    • 0001046913 scopus 로고
    • 2-pentaammine-osmium(II) complexes, see: (a) Kolis, S. P.; Gonzalez, J.; Bright, L. M.; Harman, W. D. Organometallics 1996, 15, 245. (b) Spera, M. L.; Harman, W. D. Organometallics 1995, 14, 1559. (c) Hodges, L. M.; Gonzalez, J.; Koontz, J. I.; Myers, W. H.; Harman, W. D. J. Org. Chem. 1995, 60, 2125.
    • (1995) J. Org. Chem. , vol.60 , pp. 2125
    • Hodges, L.M.1    Gonzalez, J.2    Koontz, J.I.3    Myers, W.H.4    Harman, W.D.5
  • 18
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    • (a) A solution of gaseous formaldehyde in methanol is prepared by the thermal decomposition of paraformaldehyde. (b) The synthesis and characterization of the acetaldehyde complex has been previously reported. See Harman, W. D.; Sekine, M.; Taube, H. J. Am. Chem. Soc. 1988, 110, 2439.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2439
    • Harman, W.D.1    Sekine, M.2    Taube, H.3
  • 19
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    • note
    • 2-coordinated carbonyl has been reported for 2 as 1074 cm-1, but it is obscured by N-H bending and triflate absorptions and has not been confirmed. See ref 7b.
  • 20
    • 2642709156 scopus 로고    scopus 로고
    • note
    • a of the aldehyde complexes.
  • 21
  • 25
    • 0000649646 scopus 로고    scopus 로고
    • We have observed uncoordinated oxonium carbons in this range. See: (a) Kolis, S. P.; Kopach, M. E.; Liu, R.; Harman, W. D. J. Org. Chem. 1997, 62, 130. (b) Kopach, M. E.; Gonzalez, J.; Harman, W. D. J. Am. Chem. Soc. 1991, 113, 8972.
    • (1997) J. Org. Chem. , vol.62 , pp. 130
    • Kolis, S.P.1    Kopach, M.E.2    Liu, R.3    Harman, W.D.4
  • 26
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    • We have observed uncoordinated oxonium carbons in this range. See: (a) Kolis, S. P.; Kopach, M. E.; Liu, R.; Harman, W. D. J. Org. Chem. 1997, 62, 130. (b) Kopach, M. E.; Gonzalez, J.; Harman, W. D. J. Am. Chem. Soc. 1991, 113, 8972.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8972
    • Kopach, M.E.1    Gonzalez, J.2    Harman, W.D.3
  • 28
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    • note
    • The reduction of the Os(III) precursor in the presence ot acrolein results in an unidentified paramagnetic product.
  • 37
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    • John Wiley and Sons Inc.: New York
    • For a reveiw of other methods of carbyne and alkylidyne formation, see Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; John Wiley and Sons Inc.: New York, 1988.
    • (1988) Metal-Ligand Multiple Bonds
    • Nugent, W.A.1    Mayer, J.M.2
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    • (b) Lay, P. A.; Magnuson, R. H.; Taube, H. Inorg. Synth. 1986, 24, 269. For an improved detailed procedure for the synthesis of this reagent, see: Gonzalez, J., Ph.D. Dissertation, Department of Chemistry, University of Virginia, May, 1995. This compound is currently available from Aldrich.
    • (1986) Inorg. Synth. , vol.24 , pp. 269
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  • 44
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    • Ph.D. Dissertation, Department of Chemistry, University of Virginia, May
    • (b) Lay, P. A.; Magnuson, R. H.; Taube, H. Inorg. Synth. 1986, 24, 269. For an improved detailed procedure for the synthesis of this reagent, see: Gonzalez, J., Ph.D. Dissertation, Department of Chemistry, University of Virginia, May, 1995. This compound is currently available from Aldrich.
    • (1995)
    • Gonzalez, J.1


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