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Volumn 27, Issue 14, 2008, Pages 3593-3600

Cascade reactions of dialkynyl fischer carbene complexes involving intramolecular alkyne insertions oriented to the synthesis of functionalized polycycles

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ARSENIC COMPOUNDS; CHLORINE COMPOUNDS; CYCLOADDITION; FUNCTIONAL ELECTRIC STIMULATION; SULFUR COMPOUNDS;

EID: 49349109977     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800381q     Document Type: Article
Times cited : (14)

References (58)
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    • For intramolecular alkyne insertions in Fischer carbene complexes: (a) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 116, 9873-9874.
    • For intramolecular alkyne insertions in Fischer carbene complexes: (a) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 116, 9873-9874.
  • 25
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    • For examples of cascade processes triggered by alkyne insertions on Fischer carbene complexes: (a) Harvey, D. F, Grenzer, E. M, Gantzel, P. K. J. Am. Chem. Soc. 1994, 116, 6719-6732
    • For examples of cascade processes triggered by alkyne insertions on Fischer carbene complexes: (a) Harvey, D. F.; Grenzer, E. M.; Gantzel, P. K. J. Am. Chem. Soc. 1994, 116, 6719-6732.
  • 27
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    • For recent examples of the use of trimethylsilylacetylene in intermolecular reactions with Fischer carbene complexes see: (a) Moser, W. H, Sun, L, Huffman, J. C. Org. Lett. 2001, 3, 3389-3391
    • For recent examples of the use of trimethylsilylacetylene in intermolecular reactions with Fischer carbene complexes see: (a) Moser, W. H.; Sun, L.; Huffman, J. C. Org. Lett. 2001, 3, 3389-3391.
  • 30
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    • Silylketenes have been previously prepared by intramolecular reactions of aminocarbenes: Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381-390.
    • Silylketenes have been previously prepared by intramolecular reactions of aminocarbenes: Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381-390.
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    • CCDC-680526 contains the supplementary crystallographic data for compound 12. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif.
    • CCDC-680526 contains the supplementary crystallographic data for compound 12. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif.
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    • CCDC-680527 contains the supplementary crystallographic data for compound 16a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif.
    • CCDC-680527 contains the supplementary crystallographic data for compound 16a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif.
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    • For some selected examples on DFT calculations on group 6 Fischer carbene complexes see: (a) Gleichmann, M. M.; Dòtz, K. H.; Hess, B. A. J. Am. Chem. Soc. 1996, 118, 10551-10560.
    • For some selected examples on DFT calculations on group 6 Fischer carbene complexes see: (a) Gleichmann, M. M.; Dòtz, K. H.; Hess, B. A. J. Am. Chem. Soc. 1996, 118, 10551-10560.
  • 41
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    • Geometry optimizations were carried out employing the LANL2DZ ECP for Cr and the 6-3IG* basis set for the rest of the atoms. Single-point energy calculations at the stationary points were carried out by employing the 6-311++G** basis set for H, C, O, and Si and again the LANL2DZ basis set for Cr. Solvation free energy was calculated by employing the SRCF PCM model. See the Supporting Information for further details.
    • Geometry optimizations were carried out employing the LANL2DZ ECP for Cr and the 6-3IG* basis set for the rest of the atoms. Single-point energy calculations at the stationary points were carried out by employing the 6-311++G** basis set for H, C, O, and Si and again the LANL2DZ basis set for Cr. Solvation free energy was calculated by employing the SRCF PCM model. See the Supporting Information for further details.
  • 43
    • 49349102212 scopus 로고    scopus 로고
    • The seven-membered ring could also be formed by an endo insertion of the triple bond in the chromium tetracarbonyl complex. This route was also studied, and the transition state for the endo insertion turned out to be 6.5 kcal mol-1 to higher energy than the transition state of the exo insertion gas-phase Gibbs free energy with the smaller basis set combination, Therefore, this route was discarded
    • -1 to higher energy than the transition state of the exo insertion (gas-phase Gibbs free energy with the smaller basis set combination). Therefore, this route was discarded.
  • 44
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    • -1. Therefore, for system A the reaction pathway initiated by the CO dissociation will be favoured. See (a) Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, J. Am. Chem. Soc 2004, 126, 10457-10471, See the Supporting Information for further details.
    • -1. Therefore, for system A the reaction pathway initiated by the CO dissociation will be favoured. See (a) Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, J. Am. Chem. Soc 2004, 126, 10457-10471, See the Supporting Information for further details.
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    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keit
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc., Wallingford, CT, 2004.
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    • For some recent computational work on organometallic species: a
    • For some recent computational work on organometallic species: (a) Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319-2330.
    • (2005) Organometallics , vol.24 , pp. 2319-2330
    • Kozuch, S.1    Amatore, C.2    Jutand, A.3    Shaik, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.