The tandem Diels-Alder reaction of dimethyl acetylenedicarboxylate to bicyclopentadiene. A theoretical study of the molecular mechanisms

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7573-7576

  Domingo, Luis R ^a   Arnó, Manuel ^a   Andrés, Juan ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT JAUME I   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; REACTION ANALYSIS; THEORY;

BETULACEAE;

EID: 0030583494     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01832-1     Document Type: Article

References (11)

1. (1) (a) Denmark, S.E.; Thorarensen, A. Chem. Rev. 1996, 96, 137 and references therein.
2. (b) Winkler, J.D. Chem. Rev. 1996, 96, 167 and references therein.
3. (2) (a) Sauer, J.; Sustmann, R. Angew. Chem. Int. Ed. Engl. 1980, 19, 779.
4. (b) Houk, N.K., Gonzalez J., Li, Y. Acc. Chem. Res. 1995, 28, 81.
5. (3) Domingo, L.R.; Sanz-Cervera, J.F.; Williams, R.M.; Picher, M.T.; Marco, J.A., submitted to publication.
6. (4) Paquette, L.; Wyvratt, M.; Berk, H.; Moerch, R. J. Am. Chem. Soc. 1978, 100, 5845.
7. (5) Gaussian 94, Revision B.1, Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Gill, P.M.W.; Johnson, B.G.; Robb, M.A.; Cheeseman, J.R.; Keith, T.; Petersson, G.A.; Montgomery, J.A.; Raghavachari, K.; Al-Laham, M.A.; Zakrzewski, V.G.; Ortiz, J.V.; Foresman, J.B.; Cioslowski, J.; Stefanov, B.B.; Nanayakkara, A.; Challacombe, M.; Peng, C.Y.; Ayala, P.Y.; Chen, W.; Wong, M.W.; Andres, J.L.; Replogle, E.S.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Binkley, J.S.; Defrees, D.J.; Baker, J.; Stewart, J.P.; Head-Gordon, M.; Gonzalez, C.; Pople, J.A. Gaussian, Inc. Pittsburgh PA, 1995.
8. (6) (a) Domingo, L.R.; Jones, R.A.; Picher, M.T. Sepúlveda-Arques, J. Tetrahedron 1995, 51, 8739.
9. (b) Domingo, L.R.; Jones, R.A.; Picher, M.T. Sepúlveda-Arques, J. J. Mol. Struct. (Theochem) 1996, 326, 209.
10. (c) Domingo, L.R.; Picher, M.T.; Andrés, J.; Moliner, V.; Safont, V.S., Tetrahedron 1996, in press.
11. (7) A complete theoretical study of the tandem cycloaddition of ditrifluoromethylacetylene to N-N'-dipyrrolylmethane is in progress.