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Volumn 72, Issue 3, 2007, Pages 848-860

Methylene transfer or carbometalation? A theoretical study to determine the mechanism of lithium carbenoid-promoted cyclopropanation reactions in aggregation and solvation states

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; DIMERS; LITHIUM COMPOUNDS; MONOMERS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

EID: 33846918665     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062129i     Document Type: Article
Times cited : (21)

References (61)
  • 11
    • 0031576696 scopus 로고    scopus 로고
    • Bernardi et al. also proposed another reaction pathway related to the Simmons-Smith reaction, the C-H insertion pathway to form propene
    • Bernardi, F.; Bottom, A.; Miscione, G. P. J. Am. Chem. Soc. 1997, 119, 12300-12305. Bernardi et al. also proposed another reaction pathway related to the Simmons-Smith reaction, the C-H insertion pathway to form propene.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 12300-12305
    • Bernardi, F.1    Bottom, A.2    Miscione, G.P.3
  • 56
    • 33846901065 scopus 로고    scopus 로고
    • 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.; Pople, J. A. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
  • 59
    • 33846920987 scopus 로고    scopus 로고
    • There may exist another concurrent reaction, the C-H insertion to form propene. We have located the transition state for it, and the structure of this transition state has been added to the Supporting Information. This transition state is similar to those reported by Bernardi et al, ref 10) and has a relatively high reaction barrier 27.0 kcal/mol at the B3LYP/6-311.G** level of theory, Considering that we are mainly concerned with the mechanisms that produce cyclopropanes for the lithium carbenoids, we didn't discuss it further in this paper
    • There may exist another concurrent reaction, the C-H insertion to form propene. We have located the transition state for it, and the structure of this transition state has been added to the Supporting Information. This transition state is similar to those reported by Bernardi et al. (ref 10) and has a relatively high reaction barrier (27.0 kcal/mol at the B3LYP/6-311.G* * level of theory). Considering that we are mainly concerned with the mechanisms that produce cyclopropanes for the lithium carbenoids, we didn't discuss it further in this paper.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.