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2,5-bis(trifluoromethyl)-1,3,4-oxadiazole in cycloaddition reactions

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The cycloaddition of 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole to dienophiles with cyclic and acyclic structures takes place according to a two-step mechanism with the extrusion of nitrogen and results in the formation of derivatives of 7-oxabicyclo [2.2.1]heptanes. A significant influence of the donor properties of the dienophiles, as well as of the spatial factors, on the realization of these processes has been discovered. However, solvation efects do not have a significant effect on the formation of the cycloadducts. The regio- and stereoselectivity of the cyclo-addition reactions has been noted.

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Authors
  1. N. V. Vasil'ev
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  2. Yu. E. Lyashenko
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  3. M. V. Galakhov
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  4. A. F. Kolomiets
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  5. A. F. Gontar'
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  6. G. A. Sokol'skii
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Additional information

For a preliminary report, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 95–100, January, 1990.

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Vasil'ev, N.V., Lyashenko, Y.E., Galakhov, M.V. et al. 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole in cycloaddition reactions. Chem Heterocycl Compd 26, 81–85 (1990). https://doi.org/10.1007/BF00506855

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  • DOI: https://doi.org/10.1007/BF00506855

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