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Synthesis and oxidation of sulfides containing an isocyanurate fragment

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Abstract

The reaction of 1-(ω-haloalkyl)-3,5-dimethylisocyanurates with sodium salt of methyl thioglycolate afforded the corresponding 1-[ω-(methoxycarbonylmethylthio)alkyl]-3,5-dimethylisocyanurates, the oxidation of which with the system 34% aqueous H2O2-0.2 M NaHCO3-MnII leads to the corresponding sulfones. The oxidation of these compounds with 34% aq. H2O2 in Ac2O gives alternative products, viz., sulfones, sulfoxides, or α-acyloxy sulfides, depending on the temperature and number of methylene groups between the isocyanurate fragment and the sulfur atom.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    L. F. Saifina, M. M. Shulaeva, S. G. Fattakhov, O. A. Lodochnikova, I. A. Litvinov, M. D. Zalyalyutdinova, Sh. K. Latypov & V. S. Reznik

Authors
  1. L. F. Saifina
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  2. M. M. Shulaeva
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  3. S. G. Fattakhov
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  4. O. A. Lodochnikova
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  5. I. A. Litvinov
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  6. M. D. Zalyalyutdinova
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  7. Sh. K. Latypov
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  8. V. S. Reznik
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Corresponding author

Correspondence to M. M. Shulaeva.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2528–2534, December, 2008.

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Saifina, L.F., Shulaeva, M.M., Fattakhov, S.G. et al. Synthesis and oxidation of sulfides containing an isocyanurate fragment. Russ Chem Bull 57, 2579–2585 (2008). https://doi.org/10.1007/s11172-008-0371-6

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  • DOI: https://doi.org/10.1007/s11172-008-0371-6

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