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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

Abstract

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

Keywords

Alkenes Polyunsaturated esters Site selectivity NMR spectroscopy Mass spectroscopy 

Notes

Acknowledgments

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)

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Copyright information

© Springer-Verlag Wien 2016

Authors and Affiliations

  1. 1.Institute of Industrial Organic ChemistryWarsawPoland

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