Nucleophilic replacement of the nitro group in E-2,4,6-trinitrostilbenes by O- and S-nucleophiles. Synthesis of 2-aryl-4-X-6-nitrobenzo[b]thiophenes

Russian Chemical Bulletin

Volumn 54, Issue 3, 2005, Pages 711-718

  Sapozhnikov, O Yu ^a   Mezhnev, V V ^a   Dutov, M D ^a   Kachala, V V ^a   Popov, N A ^a   Shevelev, S A ^a  

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

Author keywords

2,4,6 trinitrotoluene; Benzo b thiophenes; E 2,4,6 trinitrostilbenes; Heterocyclization; Nitro compounds; Nucleophilic substitution for the nitro group; Sulfides; Sulfones

Indexed keywords

EID: 25144475967     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-005-0309-1     Document Type: Article

References (24)

1. O. Yu. Sapozhnikov, V. V. Mezhnev, M. D. Dutov, V. V. Kachala, and S. A. Shevelev, Mendeleev Commun., 2004, 27.
2. V. A. Tartakovsky, S. A. Shevelev, M. D. Dutov, A. Kh. Shakhnes, A. L. Rusanov, L. G. Komarova, and A. M. Andrievsky, in Conversion Concepts for Commercial Applications and Disposal Technologies of Energetic Systems, Ed. H. Krause, Kluwer Academic Publishers, Dordrecht, 1997, p. 137.
3. S. A. Shevelev, V. A. Tartakovsky, and A. L. Rusanov, in Combustion of Energetic Materials, Eds K. K. Kuo and L. T. DeLuca, Begell House, Inc., New York, 2002, p. 62.
4. I. L. Dalinger, T. I. Cherkasova, S. S. Vorob'ev, A. V. Aleksandrov, G. P. Popova, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2001, 2292
5. [Russ. Chem. Bull., Int. Ed., 2001, 50, 2401].
6. T. K. Shkineva, I. L. Dalinger, S. I. Molotov, and S. A. Shevelev, Tetrahedron Lett., 2000, 41, 4973.
7. V. V. Rozhkov, A. M. Kuvshinov, V. I. Gulevskaya, I. I. Chevrin, and S. A. Shevelev, Synthesis, 1999, 2065.
8. A. M. Kuvshinov, V. I. Gulevskaya, V. V. Rozhkov, and S. A. Shevelev, Synthesis, 2000, 1474.
9. I. L. Dalinger, T. I. Cherkasova, V. M. Khutoretskii, and S. A. Shevelev, Mendeleev Commun., 2000, 72.
10. V. I. Gulevskaya, A. M. Kuvshinov, and S. A. Shevelev, Net. Commun., 2001, 7, 283.
11. E. Buncel, M. R. Crampton, M. J. Strauss, and F. Terrier, Electron Deficient Aromatic and Heteroaromatic Base Interaction. The Chemistry of Anionic Sigma-Complexes, Elsevier, New York, 1984.
12. F. Terrier, Chem. Rev., 1982, 82, 77.
13. O. V. Serushkina, M. D. Dutov, V. N. Solkan, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2001, 2297
14. [Russ. Chem. Bull., Int. Ed., 2001, 50, 2406].
15. F. Benedetti, D. R. Marshall, C. J. M. Stirling, and J. L. Leng, J. Chem. Soc., Chem. Commun., 1982, 18, 918.
16. (a) O. V. Serushkina, M. D. Dutov, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 2001, 252
17. [Russ. Chem. Bull., Int. Ed., 2001, 50, 261];
18. (b) V. N. Solkan and S. A. Shevelev, Abstrs, III Vserossiiskii simposium po organicheskoi khimii "Strategiya i taktika organicheskogo sinteza" (Yaroslavl', Rossiya, mart 2001 g.) [III All-Russia Symp. on Organic Chemistry "Strategy and Tactics of Organic Synthesis" (Yaroslavl, Russia, March, 2001)], Yaroslavl, 2001, 100 (in Russian).
19. V. V. Rozhkov, A. M. Kuvshinov, and S. A. Shevelev, Synth. Commun., 2002, 32, 1465.
20. O. V. Serushkina, M. D. Dutov, O. Yu. Sapozhnikov, B. I. Ugrak, and S. A. Shevelev, Zh. Org. Khim., 2002, 38, 1819
21. [Russ. J. Org. Chem., 2002, 38 (Engl. Transl.)].
22. E. Kuhle, Synthesis, 1970, 561.
23. A. Ruwet and M. Renson, Bull. Soc. Chim. Belg., 1970, 593.
24. S. A. Shevelev, I. L. Dalinger, and T. I. Cherkasova, Tetrahedron Lett., 2001, 42, 8539.