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Reaction of nitroalkanes with levoglucosenone and its α-bromo and α-iodo derivatives. Cyclopentaannulation of α-halocyclenones

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Abstract

Michael reactions of levoglucosenone and its α-bromo and α-iodo derivatives with α,ω-dinitroalkanes were studied under conditions of chemical and electrochemical generation of base. Procedures were developed for stereospecific fusion of a cyclopentane ring to α-bromo- and α-iodolevoglucosenones, 2-iodocyclopent-2-en-1-one, and 2-iodocyclohex-2-en-1-one by the action of 2,2-dimethyl-1,3-dinitropropane.

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Authors and Affiliations

  1. Bashkir State University, ul. Zaki Validi 32, Ufa, 450074, Bashkortostan, Russia

    L. Kh. Faizullina & M. G. Safarov

  2. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    L. V. Spirikhin, V. S. Kolosnitsyn, Yu. A. Kondrova & F. A. Valeev

Authors
  1. L. Kh. Faizullina
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  2. M. G. Safarov
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  3. L. V. Spirikhin
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  4. V. S. Kolosnitsyn
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  5. Yu. A. Kondrova
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  6. F. A. Valeev
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Correspondence to L. Kh. Faizullina.

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Original Russian Text © L.Kh. Faizullina, M.G. Safarov, L.V. Spirikhin, V.S. Kolosnitsyn, Yu.A. Kondrova, F.A. Valeev, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 6, pp. 897–902.

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Faizullina, L.K., Safarov, M.G., Spirikhin, L.V. et al. Reaction of nitroalkanes with levoglucosenone and its α-bromo and α-iodo derivatives. Cyclopentaannulation of α-halocyclenones. Russ J Org Chem 47, 914–919 (2011). https://doi.org/10.1134/S1070428011060145

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  • DOI: https://doi.org/10.1134/S1070428011060145

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