Dicationic electrophilic systems: The activation of carbocations and carboxonium ions by pyridinium groups and related heterocycles

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6841-6844

  Zhang, Yun ^a   Klumpp, Douglas A ^a  

^a CALIFORNIA STATE POLYTECHNIC UNIVERSITY   (United States)

Author keywords

Dication; Electrophile; Heterocycle; Superacid

Indexed keywords

ACID; BROMINE DERIVATIVE; CARBON; CARBOXONIUM ION; CATION; CINNAMYL BROMIDE; HETEROCYCLIC COMPOUND; INORGANIC SALT; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037119761     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01508-3     Document Type: Article

References (17)

1. (a) Giringauz, A. Medicinal Chemistry; Wiley-VHC: New York, 1997;
2. (b) Pharmaceuticals; McGuire, J. L., Ed.; Wiley-VHC: New York, 2000; Vol. 2.
3. (a) Andersson P.G., Schink H.E., Osterlund K. J. Org. Chem. 63:1998;8067.
4. (b) Rische T., Eilbracht P. Tetrahedron. 55:1999;1915.
5. Klumpp, D. A.; Aguirre, S. L.; Sanchez, G. V., Jr. Abstract of Papers, 223nd National Meeting of the American Chemical Society, Orlando, CA, April 2002; American Chemical Society: Washington, DC, 2002; Abstract ORGN 345.
6. (a) Sanchez, G. V.; Klumpp, D. A.; de Leon, S. Abstract of Papers, Pacifichem2000, Honolulu, HI, December 2000; American Chemical Society: Washington, DC, 2000; Abstract 90005894.
7. (b) Klumpp D.A., Sanchez G.V. Jr., Aguirre S.L., Zhang Y., de Leon S. J. Org. Chem. 67:2002;5028.
8. For related studies, see: (a) Klumpp, D. A. Recent Res. Dev. Org. Chem.: Part I 2001, 193; (b) Klumpp, D. A.; Aguirre, S. L.; Sanchez, G. V., Jr.; de Leon, S. J. Org. Lett. 2001, 3, 2781.
9. For related studies, see: (a) Klumpp, D. A. Recent Res. Dev. Org. Chem.: Part I 2001, 193; (b) Klumpp, D. A.; Aguirre, S. L.; Sanchez, G. V., Jr.; de Leon, S. J. Org. Lett. 2001, 3, 2781.
10. 2O is added. On cooling in a freezer, crystals of the salts (6-10) begin to appear within 1-2 days.
11. 4 and concentration gives product (11-15, purity 90-99% by NMR).
12. (a) For a review of TfOH chemistry, see: Stang P.J., White M.R. Aldrichim. Acta. 16:1983;15.
13. (b) TfOH may be quantitatively recycled. For a procedure, see: Booth B.L., El-Fekky T.A. J. Chem. Soc., Perkin Trans. 1. 1979;2441.
14. (a) Shudo, S.; Ohwada, T. In Stable Carbocation Chemistry; Prakash, G. K. S.; Schleyer, P. v. R., Eds.; Wiley: New York, 1997;
15. (b) Creary X. Chem. Rev. 91:1991;1625.
16. Olah G.A., Burrichter A., Rasul G., Yudin A.K., Prakash G.K.S. J. Org. Chem. 61:1996;1934.
17. 3).