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Volumn 73, Issue 21, 2008, Pages 8331-8336

Regio- and stereochemistry of [2 + 2] photocycloadditions of imines to alkenes: A computational and experimental study

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; HYDROCARBONS; OLEFINS; OPTICAL PROPERTIES; PHOTOREACTIVITY; PROPULSION; STEREOCHEMISTRY; STEREOSELECTIVITY;

EID: 55249106894     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8015242     Document Type: Article
Times cited : (14)

References (18)
  • 1
    • 28044466053 scopus 로고    scopus 로고
    • Griesbeck, A. G, Mattay, J, Eds, Marcel Dekker: New York
    • Fleming, S. A. In Synthetic Organic Photochemistry; Griesbeck, A. G., Mattay, J., Eds.; Marcel Dekker: New York, 2005; p 141.
    • (2005) Synthetic Organic Photochemistry , pp. 141
    • Fleming, S.A.1
  • 2
    • 55249110687 scopus 로고    scopus 로고
    • 2nd ed, Horspool, W. M, Lenci, F, Eds, CRC Press: Boca Raton, FL, Chapter 62
    • Abe, M. In CRC Handbook of Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; Chapter 62.
    • (2004) CRC Handbook of Photochemistry and Photobiology
    • Abe, M.1
  • 13
    • 55249096319 scopus 로고    scopus 로고
    • Andersson, K, Barisz, M, Bernhardsson, A, Blomberg, M. R. A, Cooper, D. L, Fleig, T, Fülscher, M. P, de Graaf, C, Hess, B. A, Karlström, G, Lindh, R, Malmqvist, P.-Å, Neogrády, P, Olsen, J, Roos, B. O, Schmmelpfennid, B, Schültz, M, Sadlej, A. J, Schütz, M, Seijo, L, Serrano-Andrés, L, Siegbahn, P. E. M, Stårling, J, Thorsteinsson, T, Veryazov, V, Widmark, P.-O. MOLCAS, version 6.4; University of Lund: Lund, Sweden, 2003
    • Andersson, K.; Barisz, M.; Bernhardsson, A.; Blomberg, M. R. A.; Cooper, D. L.; Fleig, T.; Fülscher, M. P.; de Graaf, C.; Hess, B. A.; Karlström, G.; Lindh, R.; Malmqvist, P.-Å.; Neogrády, P.; Olsen, J.; Roos, B. O.; Schmmelpfennid, B.; Schültz, M.; Sadlej, A. J.; Schütz, M.; Seijo, L.; Serrano-Andrés, L.; Siegbahn, P. E. M.; Stårling, J.; Thorsteinsson, T.; Veryazov, V.; Widmark, P.-O. MOLCAS, version 6.4; University of Lund: Lund, Sweden, 2003.
  • 14
    • 55249096788 scopus 로고    scopus 로고
    • Frisch, M. J, Tracks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery Jr, J. A, Stratmann, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Baboul, A. G, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B, Chen, W, Wong, M. W, Andres, J. L, Gonzalez, C, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 03, revision C.02; Gaussian Inc, Pittsburgh, PA, 2003
    • Frisch, M. J.; Tracks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, revision C.02; Gaussian Inc.: Pittsburgh, PA, 2003.
  • 17
    • 55249094662 scopus 로고    scopus 로고
    • The experimental outcome in the case of N-substituted olefins should be the same that the one found for O-substituted olefins, as predicted by the theoretical data. Thus, experimental exploration of the regio- and stereochemistry is well represented by methyl vinyl ether. Nevertheless, we tried to carry out the reaction with N-vinyl pyrrolidinone to further confirm the mechanism. Unfortunately, although some reaction took place, we found the product to be photoactive and no conclusive data could be obtained from the reaction mixture. Further efforts are currently under way
    • The experimental outcome in the case of N-substituted olefins should be the same that the one found for O-substituted olefins, as predicted by the theoretical data. Thus, experimental exploration of the regio- and stereochemistry is well represented by methyl vinyl ether. Nevertheless, we tried to carry out the reaction with N-vinyl pyrrolidinone to further confirm the mechanism. Unfortunately, although some reaction took place, we found the product to be photoactive and no conclusive data could be obtained from the reaction mixture. Further efforts are currently under way.


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