Endo- and exocyclic N-alkylation of 1- and 5-aminotetrazoles with t-BuOH-HClO4: synthesis of mono-, di-, and tri-tert-butyl substituted aminotetrazolium salts

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8721-8725

  Voitekhovich, Sergei V ^a   Gaponik, Pavel N ^a   Lyakhov, Alexander S ^a   Ivashkevich, Oleg A ^a  

^a BELARUSIAN STATE UNIVERSITY   (Belarus)

Author keywords

Aminotetrazoles; Quaternization; tert Butylation; Tetrazolium salts

Indexed keywords

1 AMINOTETRAZOLE DERIVATIVE; 3 TERT BUTYL 1,5 BIS(TERT BUTYLAMINO)TETRAZOLIUM PERCHLORATE; 5 AMINO 1,3 DI TERT BUTYLTETRAZOLIUM CHLORIDE; 5 AMINOTETRAZOLE DERIVATIVE; NITROGEN; TETRAZOLE DERIVATIVE; TETRAZOLIUM;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS; X RAY DIFFRACTION;

EID: 48049111170     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.095     Document Type: Article

References (31)

1. Voitekhovich S.V., Gaponik P.N., and Ivashkevich O.A. Russ. Chem. Rev. 71 (2002) 721-739
2. Gavazov K.B., Dimitrov A.N., and Lekova V.D. Russ. Chem. Rev. 76 (2007) 169-179
3. Gálvez-Ruiz J.C., Holl G., Karaghiosoff K., Klapötke T.M., Löhnwitz K., Mayer P., Nöth H., Polborn K., Rohbogner C.J., Suter M., and Weigand J.J. Inorg. Chem. 44 (2005) 4237-4253
4. Singh R.P., Verma R.D., Meshri D.T., and Shreeve J.M. Angew. Chem., Int. Ed. 45 (2006) 3584-3601
5. Fischer G., Holl G., Klapötke T.M., and Weigand J.J. Thermochim. Acta 437 (2005) 168-178
6. Klapötke T.M., Karaghiosoff K., Mayer P., Penger A., and Welch J.M. Propellants, Explos., Pyrotech. 31 (2006) 188-195
7. Wang R., Gao H., Ye C., TwamLey B., and Shreeve J.M. Inorg. Chem. 46 (2007) 932-938
8. Guo Y., Gao H., Twamley B., and Shreeve J.M. Adv. Mater. 19 (2007) 2884-2888
9. Xue H., Gao H., Twamley B., and Shreeve J.M. Chem. Mater. 19 (2007) 1731-1739
10. Zeng Z., Twamley B., and Shreeve J.M. Organometallics 26 (2007) 1782-1787
11. Ye C., Gao H., and Shreeve J.M. J. Fluorine Chem. 128 (2007) 1410-1415
12. Karaghiosoff K., Klapötke T.M., Mayer P., Sabate C.M., Penger A., and Welch J.M. Inorg. Chem. 47 (2008) 1007-1019
13. Klapötke T.M., Sabate C.M., and Rusan M. Z. Anorg. Allg. Chem. 634 (2008) 688-695
14. Klapötke T.M., and Sabate C.M. Chem. Mater. 20 (2008) 1750-1763
15. Henry R.A., Finnegan W.G., and Lieber E. J. Am. Chem. Soc. 76 (1954) 2894-2898
16. Araki S., Yamamoto K., Yagi M., Inoue T., Fukagawa H., Hattori H., Yamamura H., Kawai M., and Butsugan Y. Eur. J. Org. Chem. (1998) 121-127
17. Moderhack D., and Noreiks M. Heterocycles 63 (2004) 2605-2614
18. Moderhack D., and Holtmann B. J. Prakt. Chem. 342 (2000) 591-595
19. Voitekhovich S.V., Gaponik P.N., Lyakhov A.S., and Ivashkevich O.A. Chem. Heterocycl. Compd. 37 (2001) 949-959
20. Gaponik P.N., Voitekhovich S.V., Maruda I.I., Kulak A.A., and Ivashkevich O.A. Pol. J. Chem. 72 (1998) 2247-2253
21. Denffer M., Klapötke T.M., Kramer G., Spiess G., and Welch J.M. Propellants, Explos., Pyrotech. 30 (2005) 191-195
22. Lyakhov A.S., Voitekhovich S.V., Ivashkevich L.S., and Gaponik P.N. Acta Crystallogr. C61 (2005) o3645-o3647
23. Gaponik P.N., Voitekhovich S.V., Lyakhov A.S., Matulis V.E., Ivashkevich O.A., Quesada M., and Reedijk J. Inorg. Chim. Acta 358 (2005) 2549-2557
24. Lyakhov A.S., Gaponik P.N., and Voitekhovich S.V. Acta Crystallogr. C57 (2001) 185-186
25. Matulis V.E., Lyakhov A.S., Gaponik P.N., Voitekhovich S.V., and Ivashkevich O.A. J. Mol. Struct. 649 (2003) 309-314
26. Bocian W., Jazwinski J., Kozminski W., Stefaniak L., and Webb G.A. J. Chem. Soc., Perkin Trans. 2 (1994) 1327-1332
27. Logvinov A.V., Saraev V.V., Polyakova I.N., Strelenko Y.A., and Golod E.I. Russ. J. Gen. Chem. 77 (2007) 2186-2191
28. Allen F.H. Acta Crystallogr. B58 (2002) 380-388
29. Henry R.A., and Finnegan W.G. J. Am. Chem. Soc. 76 (1954) 923-926
30. Patent JP 59106475 A2, 1984
31. Chem. Abstr. 101 (1984) 211156