DOI QR코드

DOI QR Code

High Pressure Effects on 1,3-Dipolar Cycloaddition of Azides with Alkynes

아자이드와 알킨의 1,3-쌍극자 고리첨가반응에서 고압이 반응속도에 미치는 영향에 대한 연구

  • Kwon, Jinju (The 4th Research and Development Institute, Agency for Defense Development)
  • 권진주 (국방과학연구소 제4기술연구본부)
  • Received : 2015.06.16
  • Accepted : 2015.10.16
  • Published : 2015.12.05

Abstract

The effect of pressure on 1,3-dipolar cycloaddtion has been studied by means of FT-IR and NMR spectroscopy. Pressure accelerates 1,3-dipolar cycloaddition without solvent or catalyst. This simple and inexpensive method eliminates the need for work-up or purification. The method is expected to be applied to the synthesis of binders for solid rocket propellants.

Keywords

References

  1. Rolf Huisgen, Angew. Chem. Int. Ed., Vol. 2, No. 10, pp. 565-632, 1963. https://doi.org/10.1002/anie.196305651
  2. M. V. Gil, M. J. Arevalo, O. Lopez, Synthesis, No. 11, pp. 1589-1620, 2007.
  3. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. Barry Sharpless, Angew. Chem. Int. Ed., Vol. 41, No. 14, pp. 2596-2599, 2002. https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
  4. Morten Meldal, J. Org. Chem., Vol. 67, No. 9, pp. 3057-3064, 2002. https://doi.org/10.1021/jo011148j
  5. R. K. Iha, K. L. Wooley, A. M. Nystrom, D. J. Burke, M. J. Kade, C. J. Hawker, Chem. Rev., Vol. 109, 5620-5686, 2009 https://doi.org/10.1021/cr900138t
  6. A. J. Qin, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev., Vol. 39, pp. 2522- 2544, 2010 https://doi.org/10.1039/b909064a
  7. K. Kempe, A. Krieg, C. R. Becer, U. S. Schubert, Chem. Soc. Rev., Vol. 41, pp. 176-191, 2012. https://doi.org/10.1039/C1CS15107J
  8. Hua, A. H. Flood, Chem. Soc. Rev., Vol. 29, pp. 1262-1271, 2010
  9. A. C. Fahrenbach, J. F. Stoddart, Chem. Asian J., Vol. 6, pp. 2660-2669, 2011 https://doi.org/10.1002/asia.201100457
  10. P. A. Faugeras, B. Boens, P. H. Elchinger, F. Brouillette, D. Montplaisir, R. Zerrouki, R. Lucas, Eur. J. Org. Chem., Vol. 2012, No. 22, pp. 4087-4105, 2012. https://doi.org/10.1002/ejoc.201200013
  11. H. C. Kolb, K. B. Sharpless, DDT, Vol. 8, No. 24, pp. 1128-1137, 2003. https://doi.org/10.1016/S1359-6446(03)02933-7
  12. S. B. Otvos, I. M. Mandity, L. Kiss, F. Fulop, Chem. Asian J., Vol. 8, pp. 800-808, 2013. https://doi.org/10.1002/asia.201201125
  13. T. Keicher, W. Kuglstatter, S. Eisele, T. Wetzel, H. Krause, Propellants, Explos., Pyrotech., Vol. 34, p. 210, 2009 https://doi.org/10.1002/prep.200900001
  14. A. R. Katritzky, N. K. Meher, S. Hanci, R. Gyanda, S. R. Tala, R. S. Duran, S. Bernard, J. Polym. Sci. Part A: Polym. Chem., Vol. 46, p. 238, 2008 https://doi.org/10.1002/pola.22376
  15. B. S. Min, Y. C. Park, J. C. Yoo, Prop. Explos., Pyrotech., Accepted 2011
  16. D. Lee, K. T. Kim, Y. Jang, S. Lee, H. B. Jeon, H. Paik, B. S. Min, W. Kim, J. Appl. Polym. Sci., Vol. 131, No. 15, 2014.
  17. J. Totobenazara, A. J. Burke, Tetrahedron Letters, in Press, 2015.
  18. J. A. Shin, Y. G. Lim, K. H. Lee, J. Org. Chem., Vol. 77, pp. 4117-4122, 2012. https://doi.org/10.1021/jo3000095
  19. P. Cintas, A. Barge, S. Tagliapietra, L. Boffa, G. Cravotto, Nature Protocols, Vol. 5, No. 3, pp. 607-615, 2010. https://doi.org/10.1038/nprot.2010.1
  20. D. Ashok, D. M. Gandhi, G. Srinivas, A. V. Kumar, Med Chem Res, Vol. 23, pp. 3005-3018, 2014. https://doi.org/10.1007/s00044-013-0880-1
  21. N. J. Agard, J. A. Prescher, C. R. Bertozzi, J. Am. Chem. Soc., Vol. 126, pp. 15046-15047, 2004. https://doi.org/10.1021/ja044996f
  22. T. Keicher, W. Kuglstatter, S. Eisele, T. Wetzel, H. Krause, Propellants Explos. Pyrotech., Vol. 34, pp. 210-217, 2009. https://doi.org/10.1002/prep.200900001
  23. R. Eldik, F.G. Klarner, "High Pressure Chemistry," Wiley-VCH, Weinheim, Germany, pp. 41-66, 2002.
  24. W. J. le Noble, H. Kelm, Angew. Chem. Int. Ed. Engl., Vol. 19, p. 841, 1980. https://doi.org/10.1002/anie.198008413
  25. V. Ana, L. Gabor, K. Ernst, S. Gottfried, J.D. Paul, J. Phys. Org. Chem., Vol. 20, pp. 109-114, 2007. https://doi.org/10.1002/poc.1131
  26. G. T. Anderson, J. R. Henry, S. M. Weinreb, J. Org. Chem., Vol. 56, pp. 6946-6948, 1991. https://doi.org/10.1021/jo00024a047
  27. V. Melai, A. Brillante, P. Zanirato, J. Chem. Soc., Perkin Trans. 2, pp.2447-2449, 1998.
  28. K. Piotr, D. Krzysztof, L. Dawid, Org. Lett., Vol. 13, No. 14, pp. 3624-3627, 2011. https://doi.org/10.1021/ol201275h