Rearrangement and fluorination of quinidinone in superacid

Journal of Fluorine Chemistry

Volumn 128, Issue 1, 2007, Pages 55-59

  Chagnault, Vincent ^a   Thibaudeau, Sébastien ^a   Jouannetaud, Marie Paule ^a   Jacquesy, Jean Claude ^a   Cousson, Alain ^b   Bachmann, Christian ^c  

^a UMR 6514   (France)

^b CEA SACLAY   (France)

^c Centre National de la Recherche Scientifique   (France)

Author keywords

Carboxonium ion; Cinchona alkaloids; Fluorination; Rearrangement; Superacids

Indexed keywords

EID: 33845217652     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.09.018     Document Type: Article

References (18)

1. Jacquesy J.C. In: Prakash G.K., and Schleyer P.V.R. (Eds). Stable Carbocation Chemistry (1997), Wiley Interscience, New York 549-574 (Chapter 17)
2. Jacquesy J.C., and Fahy J. In: Torrence P.F. (Ed). Biomedical Chemistry: Applying Chemical Principles to the Understanding and Treatment of Disease: (2000), John Wiley and Sons 227-246 (Chapter 10)
3. Jacquesy J.C. In: Olah G.A., and Prakash G.K.S. (Eds). Carbocation Chemistry (2004), John Wiley and Sons, New York 359-376 (Chapter 14)
4. Thibaudeau S., Violeau B., Martin-Mingot A., Jouannetaud M.P., and Jacquesy J.C. Tetrahedron Lett. 43 (2002) 8773-8775
5. Debarge S., Thibaudeau S., Violeau B., Martin-Mingot A., Jouannetaud M.P., Jacquesy J.C., and Cousson A. Tetrahedron 61 (2005) 2065-2073
6. Debarge S., Violeau B., Jouannetaud M.P., Jacquesy J.C., and Cousson A. Tetrahedron 62 (2006) 662-671
7. Chagnault V., Jouannetaud M.P., Jacquesy J.C., and Marrot J. Tetrahedron 62 (2006) 10248-10254
8. Chagnault V., Jouannetaud M.P., and Jacquesy J.C. Tetrahedron Lett. 47 (2006) 5723-5726
9. Woodward R.B., Wendler N.L., and Brutschy F.J. J. Am. Chem. Soc. 67 (1945) 1425-1429
10. Thibaudeau S., Martin-Mingot A., Jouannetaud M.P., and Jacquesy J.C. Tetrahedron 58 (2002) 6643-6649
11. Computational details: all structures were fully optimized using the B3LYP density functional method [9]. The split valence plus polarization 6-31G(d,p) basis set was used and a vibrational analysis was performed to characterize each stationary point as a minimum or a transition state structure (zero or one imaginary vibrational frequency). Total energies were corrected for zero-point energy. The calculations were carried out with the Gaussian 98 package [10]. Structural parameters and energetic values are given in Supporting information.
12. Becke's three parameters hybrid method using the LYP correlation functional of Lee et al.
13. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
14. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
15. Frisch M.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., Baboul A.G., 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., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98, Revision A 7 (1998), Gaussian, Inc., Pittsburgh, PA
16. Gazalev A.M., Zhurinov Zh.M., Balitskii S.N., Turdybekov K.M., Shamuratov E.B., Batsnov A.S., and Struchkov Yu.T. Russ. J. Gen. Chem. 62 (1992) 758-761
17. Sheldrick G.M. SHELXS86: Program for the Solution of Crystal Structures (1985), University of Göttingen, Germany
18. Watkins D.J., Carruthers J.R., and Betteridge P.W. Crystals Software, Chemical Cristallography Laboratory (1985), University of Oxford, England