Homolytic addition of thiophenol to ethyl (Β-phenylthio)crotonate

  • T. D. Churkina
  • R. G. Petrova
  • V. I. Dostovalova
Organic Chemistry
  • 24 Downloads

Conclusions

  1. 1.

    When initiated by either peroxide or photochemically, thiophenol adds to ethyl (Β-phenylthio)crotonate to give ethyl Β,υ-bis(phenylthio)butyrate. The homolytic allylic isomerization of the unsaturated ester with hydrogen migration was postulated.

     
  2. 2.

    In contrast to the dibutylmercaptol of acetoacetic ester, the diphenylmercaptol of acetoacetic ester fails to undergo rearrangement with 1,2-migration of the phenylthio group.

     

Keywords

Hydrogen Ester Migration Peroxide Ethyl 

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Literature cited

  1. 1.
    R. G. Petrova and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 2524.Google Scholar
  2. 2.
    R. G. Petrova, T. D. Churkina, and V. I. Dostovalova, Izv. Akad. Nauk SSSR, Ser. Khim.,1979, 1818.Google Scholar
  3. 3.
    R. G. Petrova, I. I. Kandror, V. I. Dostovalova, T. D. Churkina, and R. Kh. Freidlina, Org. Magn. Reson.,11, 406 (1978).Google Scholar

Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • T. D. Churkina
    • 1
  • R. G. Petrova
    • 1
  • V. I. Dostovalova
    • 1
  1. 1.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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