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Stereochemistry of seven-membered heterocycles: XLV. Highly diastereoselective addition of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate to 2-substituted 1,3-dithiacyclohept-5-enes

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Abstract

Conformationally heterogeneous 2-substituted 1,3-dithiacyclohept-5-enes (R = Ph, Me, t-Bu), which exist in solution as chair and boat conformers, react with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with high exo-diastereoselectivity: only the chair conformer is involved. The steric structure of 4-methyl-3,5-dithia-9,10-diazabicyclo[5.4.0]undeca-7,10-diene was determined by X-ray analysis. Its crystal packing and supramolecular structure were also analyzed.

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Authors and Affiliations

  1. Butlerov Chemical Institute, Kazan State University, P.O. Box 115, Kazan, 420111, Tatarstan, Russia

    R. M. Vafina, Yu. G. Shtyrlin & E. N. Klimovitskii

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    A. T. Gubaidullin, O. N. Kataeva & I. A. Litvinov

Authors
  1. R. M. Vafina
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  2. A. T. Gubaidullin
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  3. O. N. Kataeva
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  4. I. A. Litvinov
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  5. Yu. G. Shtyrlin
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  6. E. N. Klimovitskii
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Additional information

Original Russian Text © R.M. Vafina, A.T. Gubaidullin, O.N. Kataeva, I.A. Litvinov, Yu.G. Shtyrlin, E.N. Klimovitskii, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 10, pp. 1574–1578.

For communication XLIV, see [1].

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Vafina, R.M., Gubaidullin, A.T., Kataeva, O.N. et al. Stereochemistry of seven-membered heterocycles: XLV. Highly diastereoselective addition of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate to 2-substituted 1,3-dithiacyclohept-5-enes. Russ J Org Chem 42, 1563–1567 (2006). https://doi.org/10.1134/S1070428006100277

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  • DOI: https://doi.org/10.1134/S1070428006100277

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