A theoretical study of the mechanism and stereoselectivity of the Diels-Alder cycloaddition between difluoro-2-methylencyclopropane and furan

Tetrahedron Letters

Volumn 53, Issue 43, 2012, Pages 5784-5786

  Nacereddine, Abdelmalek Khorief ^a   Yahia, Wassila ^a   Sobhi, Chafia ^a   Djerourou, Abdelhafid ^a  

^a BADJI MOKHTAR UNIVERSITY   (Algeria)

Author keywords

DFT calculations; Diels Alder cycloaddition; Molecular mechanism; Stereoselectivity

Indexed keywords

CYCLOPROPANE; DIFLUORO 2 METHYLENCYCLOPROPANE; FURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; HYDROGEN BOND; ISOMERISM; KINETICS; STEREOCHEMISTRY; THEORETICAL STUDY; THERMODYNAMICS;

ALNUS;

EID: 84866362739     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.067     Document Type: Article

References (23)

1. F. Fringuelli, and A. Taticchi Dienes in the Diels-Alder Reaction 1990 Wiley New York
2. L.A. Paquette Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Press Oxford
3. W. Dai, R. Srinivasan, and J.A. Katzenellenbogen J. Org. Chem. 54 1989 2204
4. W.R. Dolbier, M. Seabury, D. Daly, and B.E. Smart J. Org. Chem. 51 1986 974 979
5. K. Panigrahi, M. Eggen, J.-H. Maeng, Q. Shen, and D.B. Berkowitz Chem. Biol. 16 2009 928
6. J.A. Sáez, M. Arnó, and L.R. Domingo Tetrahedron 61 2005 7538 7545
7. B.S. Jursic Tetrahedron Lett. 38 1997 1305 1308
8. 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-aham, 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: Wallingford, CT, 2004.
9. A.D. Becke J. Chem. Phys. 98 1993 5648
10. A.D. Becke Phys. Rev. A 38 1988 3098
11. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
12. J.E. Carpenter, and F. Weinhold J. Mol. Struct. (THEOCHEM) 169 1988 41
13. J.P. Foster, and F. Weinhold J. Am. Chem. Soc. 102 1980 7211
14. A.E. Reed, and F. Weinhold J. Chem. Phys. 78 1983 4066
15. A.E. Reed, and F. Weinhold J. Chem. Phys. 78 1983 1736
16. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735
17. Glendening. E. D.; Reed. A. E.; Carpenter. J. E.; Weinhold. F. NBO; version 3.1 Theoretical Chemistry Institute, University of Wisconsin: Madison, 1996.
18. G. Lendvay J. Mol. Struct. (THEOCHEM) 167 1988 331
19. G. Lendvay J. Phys. Chem. 93 1989 4422
20. G. Lendvay J. Phys. Chem. 98 1994 6098
21. K.B. Wiberg Tetrahedron 24 1968 1083 1096
22. R.G. Parr, and R.G. Pearson J. Am. Chem. Soc. 105 1983 7512 7516
23. L.R. Domingo Tetrahedron 58 2002 3765 3774