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On the [4+2]-cycloaddition reaction of levoglucosenone with piperylene

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Abstract

The Diets-Alder reaction of levoglucosenone with piperylene catalyzed by ZnCl2 proceeds regio- and stereoselectively to give thesin-cis-adduct3; the thermal reaction yields an epimeric mixture of compound3 withsin-trans-adduct4 in the ratio of 4 : 1.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450005, Ufa, Russia

    F. A. Valeev, I. N. Gaisina & M. S. Miftakhov

Authors
  1. F. A. Valeev
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  2. I. N. Gaisina
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  3. M. S. Miftakhov
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Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2584–2585, October, 1996.

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Valeev, F.A., Gaisina, I.N. & Miftakhov, M.S. On the [4+2]-cycloaddition reaction of levoglucosenone with piperylene. Russ Chem Bull 45, 2453–2455 (1996). https://doi.org/10.1007/BF01435403

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  • DOI: https://doi.org/10.1007/BF01435403

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