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Geminally activated β-nitrostyrenes in reactions with cyclic β-diketones

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On the 100th anniversary of V.V. Perekalin

Abstract

The interaction of gem-benzoylnitroethenes and gem-alkoxycarbonylnitroethenes with cyclic β-diketones (dihydroresorcinol and dimedone) occurs as a one-pot process via sequential AdN and SN steps followed by denitration to give functionally substituted hexahydrobenzofurans. The intermediate products of the nucleophilic addition have been isolated in the reactions of gem-acetylnitroethenes with dihydroresorcinol. The structures of the synthesized compounds have been confirmed by IR, 1H, and 13C-{1H} spectroscopy including the heteronuclear correlation experiments (1H-13C HMQC and 1H-13C HMBC).

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Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, Moyka emb. 48, St. Petersburg, 191186, Russia

    V. M. Berestovitskaya, R. I. Baichurin, L. V. Baichurina, A. V. Fel’gendler & N. I. Aboskalova

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  1. V. M. Berestovitskaya
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  2. R. I. Baichurin
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  3. L. V. Baichurina
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  4. A. V. Fel’gendler
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  5. N. I. Aboskalova
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Correspondence to V. M. Berestovitskaya.

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Original Russian Text © V.M. Berestovitskaya, R.I. Baichurin, L.V. Baichurina, A.V. Fel’gendler, N.I. Aboskalova, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 9, pp. 1538–1546.

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Berestovitskaya, V.M., Baichurin, R.I., Baichurina, L.V. et al. Geminally activated β-nitrostyrenes in reactions with cyclic β-diketones. Russ J Gen Chem 83, 1755–1763 (2013). https://doi.org/10.1134/S1070363213090211

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  • DOI: https://doi.org/10.1134/S1070363213090211

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