Silylation of bicyclic six-membered nitronates. Ring-chain tautomerism of intermediate N,N bis(oxy)iminium cations

Russian Chemical Bulletin

Volumn 55, Issue 11, 2006, Pages 2061-2070

  Smirnov, V O ^a   Khomutova, Yu A ^a   Tishkov, A A ^a   Ioffe, S L ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Cyclic nitronates; Cycloaddition; Nitro compounds; Retroreactions; Silylation

Indexed keywords

EID: 34247165196     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-006-0549-8     Document Type: Article

References (22)

1. P. Gudax, T. K. Das Gupta, and A. Eschenmoser, Helv. Chim. Acta, 1972, 55, 2205.
2. A. A. Tishkov, H.-U. Reissig, and S. L. Ioffe, Syn. Lett., 2002, 863.
3. S. L. Ioffe, I. M. Lyapkalo, A. A. Tishkov, V. M. Danilenko, Yu. A. Strelenko, and V. A. Tartakovsky, Tetrahedron, 1997, 53, 13085.
4. A. A. Tishkov, A. V. Lesiv, Yu. A. Khomutova, Yu. A. Strelenko, I. D. Nesterov, M. Yu. Antipin, S. L. Ioffe, and S. E. Denmark, J. Org. Chem., 2003, 68, 9477.
5. Y. Tohda, N. Yamawaki, H. Matsui, T. Kawashima, M. Ariga, and Y. Mori, Bull. Chem. Soc. Jpn, 1988, 61, 461.
6. E. Shalom, J. Zenou, and S. Shatzmiller, J. Org. Chem., 1977, 42, 4213.
7. A. A. Tishkov, I. M. Lyapkalo, A. V. Kozincev, S. L. Ioffe, Yu. A. Strelenko, and V. A. Tartakovsky, Eur. J. Org. Chem., 2000, 3229.
8. M. A. Brook and D. Seebach, Can. J. Chem., 1987, 65, 836.
9. D. Seebach, I. M. Lyapkalo, and R. Dahinden, Helv. Chim. Acta, 1999, 82, 1829.
10. V. A. Tartakovsky, S. L. Ioffe, A. D. Dil'man, and A. A. Tishkov, Izv. Akad. Nauk, Ser. Khim., 2001, 1850
11. [Russ. Chem. Bull., Int. Ed., 2001, 50, 1936].
12. K. P. Birin, A. A. Tishkov, S. L. Ioffe, Yu. A. Strelenko, and V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2003, 620
13. [Russ. Chem. Bull., Int. Ed., 2003, 52, 647].
14. M. S. Klenov, A. V. Lesiv, Yu. A. Khomutova, I. D. Nesterov, and S. L. Ioffe, Synthesis, 2004, 1159.
15. J. Burfeindt, M. Patz, M. Mueller, and H. Mayr, J. Am. Chem. Soc., 1998, 120, 3629.
16. H. C. Brown and M. Borkowski, J. Am. Chem. Soc., 1952, 74, 1894.
17. V. O. Smirnov, S. L. Ioffe, A. A. Tishkov, Yu. A. Khomutova, I. D. Nesterov, M. Yu. Antipin, W. A. Smit, and V. A. Tartakovsky, J. Org. Chem., 2004, 69, 8485.
18. H. E. Gottlieb, V. Kotlyar, and A. Nudelman, J. Org. Chem., 1997, 62, 7512.
19. H. Emde, D. Domsch, H. Feger, U. Frick, A. Goetz, H. H. Hergott, K. Hofmann, W. Kober, K. Kraegeloh, T. Oesterle, W. Steppan, W. West, and G. Simchen, Synthesis, 1982, 1.
20. Organic Synthesis, Ed. H. Gilman, 2nd ed., J. Wiley and Sons, Inc., New York, 1946, CV 1, 413.
21. P. Cazeau, F. Moulines, O. Laporte, and F. Duboundin, Tetrahedron, 1987, 43, 2075.
22. L. F. Tietze and T. Eicher, Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, Georg Thieme Verlag, Stuttgart, 1991.