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Polar control in the remote oxidative functionalization of sulfones

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Oxidation of dialkyl sulfones with systems containing sodium peroxydisulfate results in remote functionalization, the site of which is dependent on the length of the alkyl chain, in agreement with polar control of this reaction by the electron-acceptor sulfonyl group.

  2. 2.

    Butyl alkyl sulfones are selectively oxidized by Na2S2O8 to 3-oxobutyl alkyl sulfones, and oxidative chlorination in the system Na2S2O8-CuCl2 gives 3- and 4-chlorobutyl alkyl sulfones, the γ-chlorination products predominating.

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Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    É. I. Troyanskii, M. I. Lazareva, D. V. Demchuk & G. I. Nikishin

Authors
  1. É. I. Troyanskii
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  2. M. I. Lazareva
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  3. D. V. Demchuk
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  4. G. I. Nikishin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2138–2144, September, 1988.

The authors thank V. E. Zubarev for obtaining and interpreting the EPR spectra.

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Troyanskii, É.I., Lazareva, M.I., Demchuk, D.V. et al. Polar control in the remote oxidative functionalization of sulfones. Russ Chem Bull 37, 1919–1925 (1988). https://doi.org/10.1007/BF00962514

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  • DOI: https://doi.org/10.1007/BF00962514

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