1,3-Dipolar cycloadditions of N-benzyl furfuryl nitrones with electron-rich alkenes

Molecules

Volumn 5, Issue 2, 2000, Pages 132-152

  Merino, Pedro ^a   Anoro, Sonia ^a   Merchan, Francisco L ^a   Tejero, Tomas ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Cycloaddition; Isoxazolidines; Nitrones; Pyrrolidines; Theoretical calculations

Indexed keywords

ALKENE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; NITRONE DERIVATIVE; PYRROLIDINE DERIVATIVE;

AB INITIO CALCULATION; CALCULATION; CHEMICAL REACTION; CONFERENCE PAPER; CYCLOADDITION; ELECTRON; THEORETICAL MODEL;

EID: 3242749241     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/50200132     Document Type: Conference Paper

References (35)

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19. The authors have deposited atomic coordinates for the structure of 2a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request, from the director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
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27. Collins, I.; Nadin, A.; Holmes, A.B.; Long, M.A.; Man, J.; Baker, R. J. Chem. Soc. Perkin Trans 1 1994, 2205. In general, electron-rich alkenes are expected to give LUMO(nitrone)-HOMO(alkene) controlled 1,3-dipolar cycloadditions. See: Seerden, J.-P. G.; Kuypers, M.M.M.; Scheeren, H.W. Tetrahedron 1995, 6, 1441 and references therein.
28. Collins, I.; Nadin, A.; Holmes, A.B.; Long, M.A.; Man, J.; Baker, R. J. Chem. Soc. Perkin Trans 1 1994, 2205. In general, electron-rich alkenes are expected to give LUMO(nitrone)-HOMO(alkene) controlled 1,3-dipolar cycloadditions. See: Seerden, J.-P. G.; Kuypers, M.M.M.; Scheeren, H.W. Tetrahedron 1995, 6, 1441 and references therein.
29. PM3 calculations were carried out using MOPAC 97 as implemented in the WINMOPAC 2.0 package (Fujitsu, 1998).
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33. Semiempirical geometry optimizations for all systems were carried out at the AM1 and PM3 levels of theory as implemented in WINMOPAC 2.0. Fujitsu Limited. 1998.
34. Ab initio calculations were performed using Gaussian 98, Revision A.3, M. Frisch, J.; Trucks, 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.; 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. and Pople, J. A. Gaussian, Inc., Pittsburgh PA, 1998.
35. The study was carried out with the N-methyl nitrone and vinyl acetate (or methyl vinyl ether). For a study of the same reaction with methyl acrylate see ref. 4b.