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

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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.

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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.

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Authors and Affiliations

  1. Institute of Industrial Organic Chemistry, Annopol 6, 3-236, Warsaw, Poland

    Mirosław Gucma, W. Marek Gołębiewski & Alicja Katarzyna Michalczyk

Authors
  1. Mirosław Gucma
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  2. W. Marek Gołębiewski
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  3. Alicja Katarzyna Michalczyk
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Corresponding author

Correspondence to W. Marek Gołębiewski.

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Gucma, M., Gołębiewski, W.M. & Michalczyk, A.K. Studies on [2 + 3] cycloaddition reaction of nitrile oxides to linear dipolarophiles bearing multiple double bonds. Monatsh Chem 147, 1809–1818 (2016). https://doi.org/10.1007/s00706-016-1797-4

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  • DOI: https://doi.org/10.1007/s00706-016-1797-4

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