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Reaction of derivatives of α-alkylthio-β-chloroisovaleric acid with ammonia

  • L. P. Rasteikene
  • V. A. Zabelaite-Mishkinene
  • É. A. Stumbrevichyute
  • M. G. Lin'kova
  • I. L. Knunyants
Organic Chemistry
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Conclusions

  1. 1.

    The replacement of chlorine by ammonia in anilides of α-alkylthio-β-chloroisovaleric acid in nitromethane, methanol, and water takes place with the formation of an episulfonium ion and results in the formation of anilides of S-alkyl-β,β-dimethylcysteine and isodimethylcysteine.

     
  2. 2.

    Methyl α-alkylthio-β-chloroisovalerates react with liquid NH3 and its solutions methanol and nitromethane according to a mechanism involving the splitting off of HCl and the addition of NH3.

     
  3. 3.

    The rate of the splitting off of HCl depends on the nature of the substituent in the alkylthio group, increasing along the series CH3S<C6H5CH2S<C6H5S.

     

Keywords

Methyl Methanol Ammonia Chlorine Solution Methanol 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    I. L. Knunyants, M. G. Lin'kova, and P. G. Ignatenok, Izv. Akad. NaukSSSR, Otd. Khim.Nauk, 54 (1955).Google Scholar
  2. 2.
    V. A. Zabelaite, L. P. Rasteikene, M. G. Lin'kova, and I.L. Knunyants, Izv. Akad. NaukSSSR, Ser. Khim., 1538 (1972).Google Scholar
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    V. A. Zabelaite, Z. A. Stumbrevichyute, L. P. Rasteikene, M. G. Lin'kova, and I. L.Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 2266 (1971).Google Scholar
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    V. A. Zabelaite, L. P. Rasteikene, M. G. Lin'kova, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1589 (1972).Google Scholar
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    L. P. Rasteikene and V. A. Mishkinene, Tr. Akad. Nauk Lit. SSR, Ser. B.,101, No. 4, 25 (1977).Google Scholar
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    A. M. Polekhin, M. K. Baranaev, N.A. Loshadkin, and S. M. Markov, Zh. Vses. Khim. O-va D. I. Mendeleeva,10, 467 (1965).Google Scholar
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    N. M. Émanuél' and D. G. Knorre, Course in Chemical Kinetics [in Russian], Moscow (1969).Google Scholar

Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • L. P. Rasteikene
    • 1
    • 2
  • V. A. Zabelaite-Mishkinene
    • 1
    • 2
  • É. A. Stumbrevichyute
    • 1
    • 2
  • M. G. Lin'kova
    • 1
    • 2
  • I. L. Knunyants
    • 1
    • 2
  1. 1.Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow
  2. 2.Institute of BiochemistryAcademy of Sciences of the Lithuanian SSRVilnius

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