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Rearrangement of radicals with 1,2-migration of chlorine during phenylation of ethyl tri and dichlorothionoacetates

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

Conclusions

  1. 1.

    The addition of phenyl radicals, generated by the decomposition of nitrosoacetanilide or benzoyl peroxide, to ethyl trichlorothionoacetate proceeds with the formation of the radical adducts CCl3C(SPh)OEt (B radicals). The latter rearrange with 1,2-migration of Cl to the CCl2C(Cl)(SPh)OEt radicals, which were identified by EPR using the spin trap technique.

  2. 2.

    Phenylation of ethyl dichlorothionoacetate followed by rearrangement of the CHCl2C (SPh)OEt radical adducts to the CHClC(Cl)(SPh)OEt takes place only when benzoyl peroxide is the source of phenyl radicals, Ph·. In the case of nitrosoacetanilide the primary radicals are stabilized by oxidation to form ethyl dichloroacetate and Ph2S2.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    R. G. Petrova, T. D. Churkina, R. G. Gasanov, B. V. Lokshin & R. Kh. Freidlina

Authors
  1. R. G. Petrova
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  2. T. D. Churkina
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  3. R. G. Gasanov
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  4. B. V. Lokshin
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  5. R. Kh. Freidlina
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 363–367, February, 1987.

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Petrova, R.G., Churkina, T.D., Gasanov, R.G. et al. Rearrangement of radicals with 1,2-migration of chlorine during phenylation of ethyl tri and dichlorothionoacetates. Russ Chem Bull 36, 323–326 (1987). https://doi.org/10.1007/BF00959374

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  • DOI: https://doi.org/10.1007/BF00959374

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