Cycloaddition reactions of dicarbonyl(η5-cyclopentadienyl)(η1-indenyl)iron

Organometallics

Volumn 15, Issue 26, 1996, Pages 5756-5758

  Kerber, Robert C ^a   Garcia, Rosa ^a   Nobre, Anthony L ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009613818     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960652p     Document Type: Article

References (30)

1. Welker, M. E. Chem. Rev. 1992, 92, 97-112.
2. Merlic, C. A.; Bendorf, H. D. Organometallics 1993, 12, 559-64 and references therein.
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4. Wright, M. E. Organometallics 1983, 2, 558-60. Wright, M. E.; Hoover, J. F.; Nelson, G. O.; Scott, C. P.; Glass, R. S. J. Org. Chem. 1984, 49, 3059-63.
5. Wright, M. E.; Hoover, J. F.; Glass, R. S.; Day, V. W. J. Organomet. Chem. 1989, 364, 373-9. Williams, J. P.; Wojcicki, A. Inorg. Chem. 1977, 16, 2506-12.
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7. Glass, R. S.; McConnell, W. W. Organometallics 1984, 3, 1630-2.
8. Lee, G.-H.; Peng, S.-M.; Yang, G.-M.; Lush, S.-F.; Liu, R.-S. Organometallics 1989, 8, 1106-11. Lee, G.-H.; Peng, S.-M.; Lush, S.-F.; Mu, D.; Liu, R-S. Organometallics 1988, 7, 1155-61.
9. Lee, G.-H.; Peng, S.-M.; Yang, G.-M.; Lush, S.-F.; Liu, R.-S. Organometallics 1989, 8, 1106-11. Lee, G.-H.; Peng, S.-M.; Lush, S.-F.; Mu, D.; Liu, R-S. Organometallics 1988, 7, 1155-61.
10. Cotton, F. A.; Musco, A.; Yagupsky, G. J. Am. Chem. Soc. 1967, 89, 6136-9. Belmont, J. A.; Wrighton, M. S. J. Organomet. Chem. 1986, 5, 1421-8.
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12. Indene reacts with TCNE very slowly in boiling acetonitrile to form a [2 + 2]-adduct: Shirota, Y.; Nagata, J.; Nakano, Y.; Nogami, T.; Mikawa, H. J. Chem. Soc., Perkin Trans. 1 1977, 14-18.
13. Formation of analogous benzonorbornenes from 1-silyl- and 1-germylindenes has been interpreted in terms of trapping of an isoindene formed by 1,2-shift of the metal moiety: Ashe, A. J., III. Tetrahedron Lett. 1970, 2105-9. Larrabee, R. B.; Dowden, B. F. Tetrahedron Lett. 1970, 915-8. Luzikov, Yu. N; Sergeyev, N. M.; Ustynyuk, Yu. A. J. Organomet. Chem. 1974, 65, 303-10. Rigby, S. S.; Girard, L.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 3798-801. However, allylsilanes and -stannanes, which cannot plausibly isomerize in this manner, readily participate in [3 + 2]-cycloadditions: Knölker, H. J.; Jones, P. G.; Pannek, J. B. Synlett 1989, 1, 429-30. Herndon, J. W.; Wu, C.; Harp, J. J.; Kreutzer, K. A. Synlett 1991, 2, 1-10. Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 3845-8. In the absence of kinetics studies to distinguish between the two possibilities, the simpler interpretation is that all of these reactions involve [3 + 2]-cycloadditions rather than prior isomerization of the metal group to C(2) of the indene.
14. Formation of analogous benzonorbornenes from 1-silyl- and 1-germylindenes has been interpreted in terms of trapping of an isoindene formed by 1,2-shift of the metal moiety: Ashe, A. J., III. Tetrahedron Lett. 1970, 2105-9. Larrabee, R. B.; Dowden, B. F. Tetrahedron Lett. 1970, 915-8. Luzikov, Yu. N; Sergeyev, N. M.; Ustynyuk, Yu. A. J. Organomet. Chem. 1974, 65, 303-10. Rigby, S. S.; Girard, L.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 3798-801. However, allylsilanes and -stannanes, which cannot plausibly isomerize in this manner, readily participate in [3 + 2]-cycloadditions: Knölker, H. J.; Jones, P. G.; Pannek, J. B. Synlett 1989, 1, 429-30. Herndon, J. W.; Wu, C.; Harp, J. J.; Kreutzer, K. A. Synlett 1991, 2, 1-10. Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 3845-8. In the absence of kinetics studies to distinguish between the two possibilities, the simpler interpretation is that all of these reactions involve [3 + 2]-cycloadditions rather than prior isomerization of the metal group to C(2) of the indene.
15. Formation of analogous benzonorbornenes from 1-silyl- and 1-germylindenes has been interpreted in terms of trapping of an isoindene formed by 1,2-shift of the metal moiety: Ashe, A. J., III. Tetrahedron Lett. 1970, 2105-9. Larrabee, R. B.; Dowden, B. F. Tetrahedron Lett. 1970, 915-8. Luzikov, Yu. N; Sergeyev, N. M.; Ustynyuk, Yu. A. J. Organomet. Chem. 1974, 65, 303-10. Rigby, S. S.; Girard, L.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 3798-801. However, allylsilanes and -stannanes, which cannot plausibly isomerize in this manner, readily participate in [3 + 2]-cycloadditions: Knölker, H. J.; Jones, P. G.; Pannek, J. B. Synlett 1989, 1, 429-30. Herndon, J. W.; Wu, C.; Harp, J. J.; Kreutzer, K. A. Synlett 1991, 2, 1-10. Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 3845-8. In the absence of kinetics studies to distinguish between the two possibilities, the simpler interpretation is that all of these reactions involve [3 + 2]-cycloadditions rather than prior isomerization of the metal group to C(2) of the indene.
16. Formation of analogous benzonorbornenes from 1-silyl- and 1-germylindenes has been interpreted in terms of trapping of an isoindene formed by 1,2-shift of the metal moiety: Ashe, A. J., III. Tetrahedron Lett. 1970, 2105-9. Larrabee, R. B.; Dowden, B. F. Tetrahedron Lett. 1970, 915-8. Luzikov, Yu. N; Sergeyev, N. M.; Ustynyuk, Yu. A. J. Organomet. Chem. 1974, 65, 303-10. Rigby, S. S.; Girard, L.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 3798-801. However, allylsilanes and -stannanes, which cannot plausibly isomerize in this manner, readily participate in [3 + 2]-cycloadditions: Knölker, H. J.; Jones, P. G.; Pannek, J. B. Synlett 1989, 1, 429-30. Herndon, J. W.; Wu, C.; Harp, J. J.; Kreutzer, K. A. Synlett 1991, 2, 1-10. Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 3845-8. In the absence of kinetics studies to distinguish between the two possibilities, the simpler interpretation is that all of these reactions involve [3 + 2]-cycloadditions rather than prior isomerization of the metal group to C(2) of the indene.
17. Formation of analogous benzonorbornenes from 1-silyl- and 1-germylindenes has been interpreted in terms of trapping of an isoindene formed by 1,2-shift of the metal moiety: Ashe, A. J., III. Tetrahedron Lett. 1970, 2105-9. Larrabee, R. B.; Dowden, B. F. Tetrahedron Lett. 1970, 915-8. Luzikov, Yu. N; Sergeyev, N. M.; Ustynyuk, Yu. A. J. Organomet. Chem. 1974, 65, 303-10. Rigby, S. S.; Girard, L.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 3798-801. However, allylsilanes and -stannanes, which cannot plausibly isomerize in this manner, readily participate in [3 + 2]-cycloadditions: Knölker, H. J.; Jones, P. G.; Pannek, J. B. Synlett 1989, 1, 429-30. Herndon, J. W.; Wu, C.; Harp, J. J.; Kreutzer, K. A. Synlett 1991, 2, 1-10. Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 3845-8. In the absence of kinetics studies to distinguish between the two possibilities, the simpler interpretation is that all of these reactions involve [3 + 2]-cycloadditions rather than prior isomerization of the metal group to C(2) of the indene.
18. Formation of analogous benzonorbornenes from 1-silyl- and 1-germylindenes has been interpreted in terms of trapping of an isoindene formed by 1,2-shift of the metal moiety: Ashe, A. J., III. Tetrahedron Lett. 1970, 2105-9. Larrabee, R. B.; Dowden, B. F. Tetrahedron Lett. 1970, 915-8. Luzikov, Yu. N; Sergeyev, N. M.; Ustynyuk, Yu. A. J. Organomet. Chem. 1974, 65, 303-10. Rigby, S. S.; Girard, L.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 3798-801. However, allylsilanes and -stannanes, which cannot plausibly isomerize in this manner, readily participate in [3 + 2]-cycloadditions: Knölker, H. J.; Jones, P. G.; Pannek, J. B. Synlett 1989, 1, 429-30. Herndon, J. W.; Wu, C.; Harp, J. J.; Kreutzer, K. A. Synlett 1991, 2, 1-10. Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 3845-8. In the absence of kinetics studies to distinguish between the two possibilities, the simpler interpretation is that all of these reactions involve [3 + 2]-cycloadditions rather than prior isomerization of the metal group to C(2) of the indene.
19. Formation of analogous benzonorbornenes from 1-silyl- and 1-germylindenes has been interpreted in terms of trapping of an isoindene formed by 1,2-shift of the metal moiety: Ashe, A. J., III. Tetrahedron Lett. 1970, 2105-9. Larrabee, R. B.; Dowden, B. F. Tetrahedron Lett. 1970, 915-8. Luzikov, Yu. N; Sergeyev, N. M.; Ustynyuk, Yu. A. J. Organomet. Chem. 1974, 65, 303-10. Rigby, S. S.; Girard, L.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 3798-801. However, allylsilanes and -stannanes, which cannot plausibly isomerize in this manner, readily participate in [3 + 2]-cycloadditions: Knölker, H. J.; Jones, P. G.; Pannek, J. B. Synlett 1989, 1, 429-30. Herndon, J. W.; Wu, C.; Harp, J. J.; Kreutzer, K. A. Synlett 1991, 2, 1-10. Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 3845-8. In the absence of kinetics studies to distinguish between the two possibilities, the simpler interpretation is that all of these reactions involve [3 + 2]-cycloadditions rather than prior isomerization of the metal group to C(2) of the indene.
20. Kamezawa, N.; Sakashita, K.; Hayamizu, K. Org. Magn. Reson. 1969, 1, 405-14 and references therein.
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23. Ashe, A. J., III. Tetrahedron Lett. 1970, 2105-9.
24. Luzikov, Yu. N.; Sergeyev, N. M.; Ustynyuk, Yu. A. J. Organomet. Chem. 1974, 65, 303-10.
25. Rigby, S. S.; Girard, L.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 3798-801.
26. Koch, H. Monatsh. Chem. 1962, 93, 1343-7. Bauer, L.; Nambury, C. N. V. J. Org. Chem. 1961, 26, 1106-10. Nelson, W. L.; Freeman, P. S. J. Org. Chem. 1975, 40, 3658-64. Eight Peak Index of Mass Spectra; Royal Society of Chemistry: London, 1983.
27. Koch, H. Monatsh. Chem. 1962, 93, 1343-7. Bauer, L.; Nambury, C. N. V. J. Org. Chem. 1961, 26, 1106-10. Nelson, W. L.; Freeman, P. S. J. Org. Chem. 1975, 40, 3658-64. Eight Peak Index of Mass Spectra; Royal Society of Chemistry: London, 1983.
28. Koch, H. Monatsh. Chem. 1962, 93, 1343-7. Bauer, L.; Nambury, C. N. V. J. Org. Chem. 1961, 26, 1106-10. Nelson, W. L.; Freeman, P. S. J. Org. Chem. 1975, 40, 3658-64. Eight Peak Index of Mass Spectra; Royal Society of Chemistry: London, 1983.
29. Koch, H. Monatsh. Chem. 1962, 93, 1343-7. Bauer, L.; Nambury, C. N. V. J. Org. Chem. 1961, 26, 1106-10. Nelson, W. L.; Freeman, P. S. J. Org. Chem. 1975, 40, 3658-64. Eight Peak Index of Mass Spectra; Royal Society of Chemistry: London, 1983.
30. Nicolet, P.; Sanchez, J.-Y.; Benaboura, A.; Abadie, M. J. M. Synthesis 1987, 202-3.