Monatshefte für Chemie - Chemical Monthly

, Volume 147, Issue 10, pp 1809–1818 | Cite as

Studies on [2 + 3] cycloaddition reaction of nitrile oxides to linear dipolarophiles bearing multiple double bonds

  • Mirosław Gucma
  • W. Marek GołębiewskiEmail author
  • Alicja Katarzyna Michalczyk
Original Paper


Site selectivity, regioselectivity, and stereoselectivity of [2 + 3] cycloaddition of benzonitrile oxides to polyunsaturated esters were examined. Site selectivity was correlated with electron charges of unsaturated carbon atoms. Structure of the products has been established by an extensive application of 1H and 13C NMR spectroscopy and electrospray ionization mass spectrometry.

Graphical abstract


Alkenes Polyunsaturated esters Site selectivity NMR spectroscopy Mass spectroscopy 



This work was supported in part by the Polish Ministry of Science and Higher Education (Research Grant NR EMC: 0150 084 31), which is gratefully acknowledged.

Supplementary material

706_2016_1797_MOESM1_ESM.pdf (1.8 mb)
Supplementary material 1 (PDF 1892 kb)


  1. 1.
    Bast K, Christl M, Huisgen R, Mack W, Sustman R (1973) Chem Ber 106:3258CrossRefGoogle Scholar
  2. 2.
    Zimmermann PJ, Blanarikova I, Juger V (2000) Angew Chem Int Ed 39:910CrossRefGoogle Scholar
  3. 3.
    Ghorai S, Mukhopadhyay R, Kundu AP, Bhattacharjya A (2005) Tetrahedron 61:2999CrossRefGoogle Scholar
  4. 4.
    Caramella P, Grunanger P (1984) In: Padwa A (ed) 1,3-Dipolar cycloaddition chemistry. Wiley, New York, p 177Google Scholar
  5. 5.
    Mukayama T, Hoshino T (1960) J Am Chem Soc 82:5339CrossRefGoogle Scholar
  6. 6.
    Shimizu T, Hayashi T, Shibafuchi H, Teramura K (1986) Bull Chem Soc Jpn 59:2827CrossRefGoogle Scholar
  7. 7.
    Gothelf KV, Jørgensen KA (1998) Chem Rev 98:863CrossRefGoogle Scholar
  8. 8.
    Pellisier H (2007) Tetrahedron 63:3235CrossRefGoogle Scholar
  9. 9.
    Kissane M, Maguire AR (2010) Chem Soc Rev 39:845CrossRefGoogle Scholar
  10. 10.
    Kanemasa S, Nishiuchi M, Kamimura A, Hori K (1994) J Am Chem Soc 116:2324CrossRefGoogle Scholar
  11. 11.
    Kheruze YI, Galishev VA, Petrov AA (1988) Zh Org Khim 24:944Google Scholar
  12. 12.
    Taylor RE, Hearn BR, Ciavarri JP (2002) Org Lett 4:2953CrossRefGoogle Scholar
  13. 13.
    Hwang SH, Kurth MJ (2002) Tetrahedron Lett 43:53CrossRefGoogle Scholar
  14. 14.
    Ong CW, Chien T-L (1996) Organometallics 15:1323CrossRefGoogle Scholar
  15. 15.
    Fisera L, Ondrus V, Timpe HJ (1990) Collect Czech Chem Commun 55:512CrossRefGoogle Scholar
  16. 16.
    Gucma M, Gołębiewski WM, Krawczyk M (2013) J Braz Chem Soc 24:805Google Scholar
  17. 17.
    Gucma M, Gołębiewski WM, Michalczyk AK (2014) J Mol Struct 1060:223CrossRefGoogle Scholar
  18. 18.
    Gucma M, Gołębiewski WM, Michalczyk AK (2016) J Braz Chem Soc. doi: 10.5935/0103-5053.20160078 Google Scholar
  19. 19.
    Gucma M, Gołębiewski WM (2011) Catal Sci Technol 1:1354CrossRefGoogle Scholar
  20. 20.
    Gucma M, Gołębiewski WM, Krawczyk M (2015) RSC Adv 5:13112CrossRefGoogle Scholar
  21. 21.
    Gerdes JM, Norman AW, Okamura WH (1981) J Org Chem 46:599CrossRefGoogle Scholar
  22. 22.
    Mouriño A, Blair P, Wecksler W, Norman AW, Okamura WH (1978) J Med Chem 21:1025CrossRefGoogle Scholar
  23. 23.
    Liu KC, Shelton BR, Howe RK (1980) J Org Chem 45:3916CrossRefGoogle Scholar
  24. 24.
    Hyperchem 7.5. Hypercube company, Gainesville, Florida, 32601 USAGoogle Scholar
  25. 25.
    McNulty J, Steere JA, Wolf S (1998) Tetrahedron Lett 39:8013CrossRefGoogle Scholar
  26. 26.
    Houk KH, Sims J, Watts CR, Jenkins LJ (1973) J Am Chem Soc 95:7301CrossRefGoogle Scholar
  27. 27.
    Raimondi L (1997) Gazz Chim Ital 127:167Google Scholar
  28. 28.
    Lewis FD, Howard DK, Barancyk SV, Oxman JD (1986) J Am Chem Soc 108:3016CrossRefGoogle Scholar
  29. 29.
    Lau KCY, Chiu P (2011) Tetrahedron 67:8769CrossRefGoogle Scholar
  30. 30.
    Comenskey DJ, Rowan DD, Matich AJ (2006) J Label Compd Radiopharm 49:47CrossRefGoogle Scholar
  31. 31.
    Khomenko TM, Tatarova LE, Korchagina DV, Barthash VA (2002) Russ J Org Chem 38:498CrossRefGoogle Scholar
  32. 32.
    Curci R, Detomaso A, Prencipe T, Carpenter GB (1994) J Am Chem Soc 116:8112CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2016

Authors and Affiliations

  1. 1.Institute of Industrial Organic ChemistryWarsawPoland

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