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Volumn 101, Issue 5, 2001, Pages 1205-1227

Metallabenzenes

Author keywords

[No Author keywords available]

Indexed keywords

METALLABENZENES;

EID: 0035353518     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr990337n     Document Type: Review
Times cited : (350)

References (72)
  • 4
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    • John Wiley and Sons: New York
    • (c) Garratt, P.J. Aromaticity; John Wiley and Sons: New York, 1986.
    • (1986) Aromaticity
    • Garratt, P.J.1
  • 6
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    • John Wiley and Sons: New York
    • "High thermodynamic stability" simply means more stable than the canonical form of lowest energy. It does not imply stability to air, light, or common reagents. See: March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons: New York, 1985; pp 37-39.
    • (1985) Advanced Organic Chemistry, 3rd ed. , pp. 37-39
    • March, J.1
  • 14
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    • (e) Bleeke, J.R.; Hinkle, P.V. J. Am. Chem. Soc. 1999, 121, 595-596. For a good theoretical discussion, see: Palmer, M.; Carter, K.; Harris, S. Organometallics 1997, 16, 2448-2459.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 595-596
    • Bleeke, J.R.1    Hinkle, P.V.2
  • 15
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    • (e) Bleeke, J.R.; Hinkle, P.V. J. Am. Chem. Soc. 1999, 121, 595-596. For a good theoretical discussion, see: Palmer, M.; Carter, K.; Harris, S. Organometallics 1997, 16, 2448-2459.
    • (1997) Organometallics , vol.16 , pp. 2448-2459
    • Palmer, M.1    Carter, K.2    Harris, S.3
  • 18
    • 0000018748 scopus 로고    scopus 로고
    • Waller, K.J.; Filippov, I.; Briggs, P.M.; Wigley, D.E. Organometallics 1998, 17, 322-329. For an example of a metallapyrimidine, see: Feng, S.G.; White, P.S.; Templeton, J.L. Organometallics 1993, 12, 1765-1774.
    • (1998) Organometallics , vol.17 , pp. 322-329
    • Waller, K.J.1    Filippov, I.2    Briggs, P.M.3    Wigley, D.E.4
  • 19
    • 0001489011 scopus 로고
    • Waller, K.J.; Filippov, I.; Briggs, P.M.; Wigley, D.E. Organometallics 1998, 17, 322-329. For an example of a metallapyrimidine, see: Feng, S.G.; White, P.S.; Templeton, J.L. Organometallics 1993, 12, 1765-1774.
    • (1993) Organometallics , vol.12 , pp. 1765-1774
    • Feng, S.G.1    White, P.S.2    Templeton, J.L.3
  • 23
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    • A similar conclusion has been reached by using molecular hardness as a criterion for aromaticity. See: Chamizo, J.A.; Morgado, J.; Sosa, P. Organometallics 1993, 12, 5005-5007.
    • (1993) Organometallics , vol.12 , pp. 5005-5007
    • Chamizo, J.A.1    Morgado, J.2    Sosa, P.3
  • 34
    • 0011690023 scopus 로고    scopus 로고
    • note
    • These same products are obtained under classical Friedel-Crafts conditions.
  • 47
    • 0011625243 scopus 로고    scopus 로고
    • note
    • 3-cyclopropenyl-metal complex upon addition of the alkyne and that the alkyne inserts into a M-cyclopropenyl σ-bond. The resulting β-cyclopropenylvinyl complex then rearranges to the observed cyclopentadienyl product.
  • 50
    • 0001575826 scopus 로고
    • These kinds of intermediates had originally been suggested by Hughes and also by Bleeke in a related iridium system. See: (a) Egan, J.W., Jr.; Hughes, R.P.; Rheingold, A.L. Organometallics 1987, 6, 1578-1581. (b) Bleeke, J.R.; Peng, W.-J. Organometallics 1987, 6, 1576-1578.
    • (1987) Organometallics , vol.6 , pp. 1578-1581
    • Egan J.W., Jr.1    Hughes, R.P.2    Rheingold, A.L.3
  • 51
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    • These kinds of intermediates had originally been suggested by Hughes and also by Bleeke in a related iridium system. See: (a) Egan, J.W., Jr.; Hughes, R.P.; Rheingold, A.L. Organometallics 1987, 6, 1578-1581. (b) Bleeke, J.R.; Peng, W.-J. Organometallics 1987, 6, 1576-1578.
    • (1987) Organometallics , vol.6 , pp. 1576-1578
    • Bleeke, J.R.1    Peng, W.-J.2
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    • 0003023530 scopus 로고
    • Thermal conversion of pentadienyl ligands to cyclopentadienyl ligands with hydrogen elimination is also known. (a) Mann, B.E.; Manning, P.; Spencer, C.M. J. Organomet. Chem. 1986, 312, C64-C66. (b) Kirss, R.U. Organometallics 1992, 11, 497-499. (c) Kirss, R.U.; Quazi, A.; Lake, C.H.; Churchill, M.R. Organometallics 1993, 12, 4145-4150.
    • (1986) J. Organomet. Chem. , vol.312
    • Mann, B.E.1    Manning, P.2    Spencer, C.M.3
  • 60
    • 0011690823 scopus 로고
    • Thermal conversion of pentadienyl ligands to cyclopentadienyl ligands with hydrogen elimination is also known. (a) Mann, B.E.; Manning, P.; Spencer, C.M. J. Organomet. Chem. 1986, 312, C64-C66. (b) Kirss, R.U. Organometallics 1992, 11, 497-499. (c) Kirss, R.U.; Quazi, A.; Lake, C.H.; Churchill, M.R. Organometallics 1993, 12, 4145-4150.
    • (1992) Organometallics , vol.11 , pp. 497-499
    • Kirss, R.U.1
  • 61
    • 0001680777 scopus 로고
    • Thermal conversion of pentadienyl ligands to cyclopentadienyl ligands with hydrogen elimination is also known. (a) Mann, B.E.; Manning, P.; Spencer, C.M. J. Organomet. Chem. 1986, 312, C64-C66. (b) Kirss, R.U. Organometallics 1992, 11, 497-499. (c) Kirss, R.U.; Quazi, A.; Lake, C.H.; Churchill, M.R. Organometallics 1993, 12, 4145-4150.
    • (1993) Organometallics , vol.12 , pp. 4145-4150
    • Kirss, R.U.1    Quazi, A.2    Lake, C.H.3    Churchill, M.R.4
  • 69
    • 0001081297 scopus 로고
    • Related reactions involving 1,3-ditungstenacyclobutadienes and alkynes have been studied. However, in these cases, a much more severe distortion is observed, leading to a structure best described as containing a dimetalated allyl ligand: Chisholm, M.H.; Huffman, J.C.; Heppert, J.A. J. Am. Chem. Soc. 1985, 107, 5116-5136. See also: Chisholm, M.H.; Jansen, R.-M.; Huffman, J.C. Organometallics 1992, 11, 2305-2307.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 5116-5136
    • Chisholm, M.H.1    Huffman, J.C.2    Heppert, J.A.3
  • 70
    • 0000514229 scopus 로고
    • Related reactions involving 1,3-ditungstenacyclobutadienes and alkynes have been studied. However, in these cases, a much more severe distortion is observed, leading to a structure best described as containing a dimetalated allyl ligand: Chisholm, M.H.; Huffman, J.C.; Heppert, J.A. J. Am. Chem. Soc. 1985, 107, 5116-5136. See also: Chisholm, M.H.; Jansen, R.-M.; Huffman, J.C. Organometallics 1992, 11, 2305-2307.
    • (1992) Organometallics , vol.11 , pp. 2305-2307
    • Chisholm, M.H.1    Jansen, R.-M.2    Huffman, J.C.3


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