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Volumn , Issue 18, 2008, Pages 3200-3208

Diels-Alder reactions of symmetrically 1,4-disubstituted dienes: Theoretical study on the influence of the configuration of the double bonds on the regioand endoselectivity

Author keywords

Cycloaddition; Density functional calculations; Diels Alder reaction; Regioselectivity

Indexed keywords


EID: 53749108069     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701082     Document Type: Article
Times cited : (6)

References (47)
  • 5
    • 0343434392 scopus 로고    scopus 로고
    • Various routes are known including thermal opening of cyclobutenes: a H. Meister, Chem. Ber. 1963, 96, 1688-1696;
    • Various routes are known including thermal opening of cyclobutenes: a) H. Meister, Chem. Ber. 1963, 96, 1688-1696;
  • 9
    • 0011651254 scopus 로고    scopus 로고
    • Wittig-type reactions: e R. K. Boeckman Jr, T. M. Dolak, K. O. Culos, J. Am. Chem. Soc. 1978, 100, 7098-7100;
    • Wittig-type reactions: e) R. K. Boeckman Jr, T. M. Dolak, K. O. Culos, J. Am. Chem. Soc. 1978, 100, 7098-7100;
  • 12
    • 0013617626 scopus 로고    scopus 로고
    • Isomerization: h H. Hiranuma, S. I. Miller, J. Org. Chem. 1983, 48, 3096-3102.
    • Isomerization: h) H. Hiranuma, S. I. Miller, J. Org. Chem. 1983, 48, 3096-3102.
  • 13
    • 84984062806 scopus 로고    scopus 로고
    • Miscellaneous methods: i J. W. Scheeren, A. T. M. Marcelis, R. W. Aben, R. J. F. Nivard, Recueil Trav. Chim. Pays-Bas 1975, 94, 196-202;
    • Miscellaneous methods: i) J. W. Scheeren, A. T. M. Marcelis, R. W. Aben, R. J. F. Nivard, Recueil Trav. Chim. Pays-Bas 1975, 94, 196-202;
  • 17
    • 53749084716 scopus 로고    scopus 로고
    • Note that the term regioselectivity is somewhat degenerate for reactions involving (E,Z)-1,4-homodisubstituted dienes, as the endo approach on one given regioisomer leads to the same adduct as the exo approach on the other regioisomer. This ambiguity was alleviated during the experimental work by assuming that a reversal from a fully endo to a fully exo selectivity going from diene 2 to diene 3 was unlikely. Obviously, this problem does not concern the present theoretical study.
    • Note that the term regioselectivity is somewhat degenerate for reactions involving (E,Z)-1,4-homodisubstituted dienes, as the endo approach on one given regioisomer leads to the same adduct as the exo approach on the other regioisomer. This ambiguity was alleviated during the experimental work by assuming that a reversal from a fully endo to a fully exo selectivity going from diene 2 to diene 3 was unlikely. Obviously, this problem does not concern the present theoretical study.
  • 19
    • 53749094090 scopus 로고    scopus 로고
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004.
  • 31
    • 0001741863 scopus 로고    scopus 로고
    • L. M. Stephenson, D. E. Smith, S. P. Current, J. Org. Chem. 1982, 47, 4170-4171.
    • c) L. M. Stephenson, D. E. Smith, S. P. Current, J. Org. Chem. 1982, 47, 4170-4171.


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