Formation and reactivity of gem-difluoro-substituted pyridinium ylides: Experimental and DFT investigation

Journal of Fluorine Chemistry

Volumn 132, Issue 3, 2011, Pages 175-180

  Kobylianskii, Ilia J ^a   Novikov, Mikhail S ^a   Khlebnikov, Alexander F ^a  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

Carbenes; Dipolar cycloaddition; Indolizines; Pyridines; Ylides

Indexed keywords

EID: 79952443097     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2010.12.013     Document Type: Article

References (29)

1. R.W. Fessenden, and R.H. Schuler J. Chem. Phys. 43 1965 2704 2712
2. K.S. Chen, P.J. Krusic, P. Meakin, and J. Kochi J. Phys. Chem. 78 1974 2014 2030
3. D.A. Dixon J. Phys. Chem. 90 1986 54 56
4. E.A. Carter, and W.A. Goddard III J. Chem. Phys. 92 1988 1752 1763
5. D.L.S. Brahms, and W.P. Dailey Chem. Rev. 96 1996 1585 1635
6. A.F. Khlebnikov, M.S. Novikov, S.A. Dolgikh, and J. Magull ARKIVOC ix 2008 94 115
7. A.S. Konev, M.S. Novikov, and A.F. Khlebnikov Tetrahedron Lett. 46 2005 8337 8340
8. A.F. Khlebnikov, M.S. Novikov, and R.R. Kostikov Russ. Chem. Rev. 74 2005 171 192
9. A.F. Khlebnikov, and R.R. Kostikov Chem. Heterocycl. Comp. 23 1987 708 709
10. A.F. Khlebnikov, E.I. Kostik, R.R. Kostikov, and V.Ya. Bespalov Chem. Heterocycl. Comp. 1990 304 311
11. A.F. Khlebnikov, E.I. Kostik, J. Kopf, E.V. Aleksandrov, and R.R. Kostikov Russ. J. Org. Chem. 34 1998 712 724
12. A.F. Khlebnikov, E.I. Kostik, and R.R. Kostikov Synthesis 25 1993 568 570
13. B. Bachowska Monatsh. Chem. 126 1995 227 231
14. K. Berg-Nielson Acta Chem. Scand., Ser. B B31 1977 224 226
15. A.F. Khlebnikov, E.I. Kostik, and R.R. Kostikov Chem. Heterocycl. Comp. 1991 636 642
16. R.A. Moss, L. Wang, and K. Krogh-Jespersen J. Am. Chem. Soc. 131 2009 2128 2130
17. G. Bissky, V.I. Staninets, A.A. Kolomeitsev, and G.-V. Röschenthaler Synlett 12 2001 374 378
18. G. Bissky, G.-V. Röschenthaler, E. Lork, J. Barten, M. Mádebielle, V. Staninets, and A.A. Kolomeitsev J. Fluorine Chem. 109 2001 173 181
19. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
20. A.D. Becke Phys. Rev. A 38 1998 3098 3100
21. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1998 785 789
22. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision B.05 2004 Gaussian Inc. Wallingford, CT
23. C. Gonzalez, and H.B. Schlegel J. Chem. Phys. 90 1989 2154 2161
24. A.F. Khlebnikov, and M.S. Novikov Russ. J. Gen. Chem. 80 2010 1341 1354
25. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165 195
26. A. Fisher, G.J. Leary, R.D. Topsom, and J. Vaughan J. Chem. Soc. 1966 782 785
27. M.S. Novikov, A.F. Khlebnikov, and M.V. Shevchenko J. Fluorine Chem. 123 2003 177 181
28. M.S. Novikov, A.F. Khlebnikov, E.S. Sidorina, and R.R. Kostikov J. Chem. Soc., Perkin Trans. 1 2000 231 237
29. J. Attenburrow, A.F.B. Cameron, J.H. Chapman, R.M. Evans, B.A. Hems, A.B.A. Jansen, and T. Walker J. Chem. Soc. 1952 1094 1112