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Stereochemistry of seven-membered heterocycles: XLVII. Synthesis, NMR, XRD, and theoretical investigation of monosulfoxides of (Z)-4,7-dihydro-1λ4,3-dithiepine series

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Abstract

By oxidation of (Z)-4,7-dihydro-1,3-dithiepines with meta-chloroperbenzoic acid the corresponding 4,7-dihydro-1λ4,3-dithiepine 1-oxides were synthesized in ∼85% yield. A complete assignment of signals in the 1H and 13C NMR spectra of the compounds obtained was established. According to XRD analysis the seven-membered heterocycles crystallized in conformations chair or boat. The calculations by DFT method in the B3LYP/6-31G(d,p) version showed the possibility of conformational equilibrium of these forms in the gas phase.

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Authors and Affiliations

  1. Butlerov Chemical Institute at Kazan State University, Kazan, 420111, Russia

    A. N. Galyautdinova, R. M. Vafina, S. G. Gnevashev, V. V. Gavrilov, Yu. G. Shtyrlin, G. A. Chmutova & E. N. Klimovitskii

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

    O. N. Kataeva & O. A. Lodochnikova

  3. Zavoiskii Physico-Technical Institute, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

    O. I. Gnezdilov

Authors
  1. A. N. Galyautdinova
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  2. R. M. Vafina
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  3. O. N. Kataeva
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  4. O. A. Lodochnikova
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  5. S. G. Gnevashev
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  6. O. I. Gnezdilov
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  7. V. V. Gavrilov
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  8. Yu. G. Shtyrlin
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  9. G. A. Chmutova
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  10. E. N. Klimovitskii
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Correspondence to E. N. Klimovitskii.

Additional information

Original Russian Text © A.N. Galyautdinova, R.M. Vafina, O.N. Kataeva, O.A. Lodochnikova, S.G. Gnevashev, O.I. Gnezdilov, V.V. Gavrilov, Yu.G. Shtyrlina, G.A. Chmutova, E.N. Klimovitskii, 2009, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 2, pp. 252–257.

For Communication XLVI, see [1].

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Galyautdinova, A.N., Vafina, R.M., Kataeva, O.N. et al. Stereochemistry of seven-membered heterocycles: XLVII. Synthesis, NMR, XRD, and theoretical investigation of monosulfoxides of (Z)-4,7-dihydro-1λ4,3-dithiepine series. Russ J Org Chem 46, 246–251 (2010). https://doi.org/10.1134/S107042801002017X

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  • DOI: https://doi.org/10.1134/S107042801002017X

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