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Reactions of diazoalkanes with unsaturated compounds 16. Catalytic reactions of diazomethane with 2-alkenyl-1,3-oxazolidines and 2-alkenyl-1,3-oxathiolanes

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Abstract

The influence of 1,3-oxazolidine and 1,3-oxathiolane fragments in substituted alkenes on the direction of their catalytic reaction with diazomethane has been investigated. The olefins bearing an oxazolidine substituent in the α- or γ-position and an oxathiolane substituent in the γ-position relative to the C=C bond react with diazomethane in the presence of Pd(acac)2 selectively resulting in cyclopropanation products. The use of Cu(OTf)2 does not result in cyclopropanation; however Cu(OTf)2 catalyzes the reaction of diazomethane with 2-(alk-1-enyl)-1,3-oxathiolanes yielding 2,3,5,6-tetrahydro-1,4-oxathiocines formed through the [2,3]-sigmatropic rearrangement of the intermediate sulfonium ylides.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    M. D. Khanova, R. M. Sultanova, R. R. Rafikov, I. P. Baykova, R. Z. Biglova & V. A. Dokichev

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    Yu. V. Tomilov

Authors
  1. M. D. Khanova
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  2. R. M. Sultanova
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  3. R. R. Rafikov
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  4. I. P. Baykova
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  5. R. Z. Biglova
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  6. V. A. Dokichev
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  7. Yu. V. Tomilov
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Corresponding author

Correspondence to M. D. Khanova.

Additional information

For Part 15 see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 604–608, March, 2008.

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Khanova, M.D., Sultanova, R.M., Rafikov, R.R. et al. Reactions of diazoalkanes with unsaturated compounds 16. Catalytic reactions of diazomethane with 2-alkenyl-1,3-oxazolidines and 2-alkenyl-1,3-oxathiolanes. Russ Chem Bull 57, 617–621 (2008). https://doi.org/10.1007/s11172-008-0097-5

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  • DOI: https://doi.org/10.1007/s11172-008-0097-5

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