About the timing of Wagner-Meerwein and Nametkin rearrangements, 6,2- hydride shift, proton elimination and cation trapping in 2-norbornyl carbocations

Tetrahedron

Volumn 54, Issue 18, 1998, Pages 4607-4614

  Martínez, Antonio García ^a   Vilar, Enrique Teso ^b   Fraile, Amelia García ^b   Fernández, Antonio Herrera ^a   De La Moya Cerero, Santiago ^a   Jiménez, Florencio Moreno ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; NITRILE; NORBORNANE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032580338     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00176-8     Document Type: Article

References (24)

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2. 2) Martínez, A.G.; Espada, I; Teso, E., Synthesis 1979, 382.
3. 3) Martínez, A. G.; Teso, E.; Osío, J.; Manrique, J.; Rodríguez, M. E.; Hanack, M.; Subramanian, L. R. Tetrahedron Lett. 1992, 33, 607.
4. 4) Martínez, A.G.; Teso, E.; García, A.; de la Moya, S.; Martínez, P.; Subramanian, L.R., Tetrahedron: Asymmetry 1996, 7, 1257.
5. 5) Martínez, A.G.; Teso, E.; García, A.; de la Moya, S.; Subramanian, L.R., Synlett 1994, 563.
6. 6) Martínez, A.G.; Teso, E.; García, A.; de la Moya, S.; Rodríguez, M.E.; Martínez, P.; Subramanian, L.R.; Gancedo, A.G., J. Med. Chem. 1995, 38, 4474.
7. 7) Martínez, A.G.; Teso, E.; García, A.; de la Moya, S.; Martínez, P.; Subramanian, L.R., Tetrahedron: Asymmetry 1996, 7, 2177.
8. 8) Martínez, A.G.; Subramanian, L.R.; Hanack, M in: "Encyclopaedia of Reagents for Organic Synthesis", Vol. 7, p. 5146; Paquette, L.A. Ed.; Wiley, New York, 1995.
9. 9) Martínez, A.G.; Herrera, A.; Moreno, F.; García, A.; Subramanian, L.R.; Hanack, M., J. Org. Chem. 1992, 57, 1628.
10. 10) Martínez, A.G.; Herrera, A.; Moreno, F.; Muñoz, P.; Alonso, C.; Subramanian, L.R., Tetrahedron. 1996, 52, 7973.
11. 11) Martínez, A.G.; Álvarez, R.M.; Teso, E.; García, A.; Hanack, M.; Subramanian, L.R., Tetrahedron Lett. 1989, 30, 581.
12. 12) (a) Brown, H.C.; Schleyer, P.v.R.: "The Nondassical Ion Problem", Plenum Press, New York, 1977.
13. (b) Kirmse, W. Acc. Chem. Res. 1986, 19, 36.
14. 13) For related compounds, see: (a) Sewald, N.; Wendisch, V., Tetrahedron: Asymmetry 1996, 7, 1269.
15. (b) Lopez, M.; Jagerovic, N.; Ballesteros, P., Tetrahedron: Asymmetry 1994, 5, 1987.
16. 14) For reviews, see: (a) Yamamoto, Y.; Sasaki, N. in "Stereochemistry of Organometallic and Inorganic Compounds" Bermal, I. Ed., Eisevier, Amsterdam, 1990, Vol. 4.
17. (b) Morrison, J.D. Ed. "Asymmetric Synthesis", Wiley, New York, 1985.
18. 15) Lenoir, D.; Apeloig, Y.; Arad, P.; Schleyer, P.v.R., J. Org. Chem. 1988, 53, 661.
19. 16) Money, T.; Palme, M.H., Tetrahedron: Asymmetry 1993, 4, 2363.
20. 2, a relationship between k and d is expected.
21. 18) Whittaker, D. in "Chemistry of Terpenes and Terpenoîds", Newman A. A. Ed., Academic Press, London, 1972.
22. 19) Martínez, A. G.; Osío, J.; Rodríguez, M.E.; Iglesias, M.; Teso, E.; Subramanian, L. R. Tetrahedron Lett. 1994, 35, 1793.
23. 13C-NMR-Spektroskopie", Thieme, Stuttgart, 1984.
24. 21) Martínez, A. G.; Teso, E.; García, A.; de la Moya, S.; Martínez, P.; Subramanian, L. R. Tetrahedron: Asymmetry 1996, 7, 2177.