The nucleophilic substitution of chlorine in derivatives ofβ-chloro-α-methylthioisovaleric acid

  • V. A. Zabelaite
  • L. P. Rasteikene
  • M. G. Lin'kova
  • I. L. Knunyants
Organic and Biological Chemistry
  • 31 Downloads

Conclusions

  1. 1.

    The nucleophilic replacement of the chlorine atoms in derivatives ofβ-chloro-α-methylthioisovaleric acid takes place through an intermediate episulfonium ion with the formation of derivatives of a single isomer ofβ-hydroxy-α-methylthioisovaleric acid derivative in each case.

     
  2. 2.

    With SOCl2 or PCl5, the methyl ester and anilide ofβ-hydroxy-α-methylsulfonylisovaleric acid eliminate Water with the formation of the methyl ester and anilide of 2-methylsulfonyl-3-methylbut-3-enoic acid.

     
  3. 3.

    The methyl ester and anilide ofβ-chloro-α-methylsulfonylisovaleric acid eliminate HC1 with the formation of the corresponding derivatives ofβ,β-dimethyl-α-methylsulfonylacrylic acid.

     

Keywords

Methyl Ester Chlorine Methyl Ester Acid Derivative 

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Literature cited

  1. 1.
    W. H. Mueller, Angew. Chem., Internat. Edit.,8, 482 (1969); M. V. A. Baig and L. N. Owen, J. Chem. Soc., 1400 (1967).Google Scholar
  2. 2.
    W. H. Mueller and P. E. Butler, J. Amer. Chem. Soc.,90, 2075 (1968).Google Scholar
  3. 3.
    L. P. Rasteikene, D. I. Greichute, M. G. Lin'kova, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 448 (1972).Google Scholar
  4. 4.
    V. A. Zabelaite, Z. A. Stumbrevichute, L. P. Rasteikene, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 2266 (1971).Google Scholar
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    L. J. Smith and L. J. Spillane, J. Amer. Chem. Soc.,65, 288 (1943).Google Scholar

Copyright information

© Consultants Bureau 1973

Authors and Affiliations

  • V. A. Zabelaite
    • 1
    • 2
  • L. P. Rasteikene
    • 1
    • 2
  • M. G. Lin'kova
    • 1
    • 2
  • I. L. Knunyants
    • 1
    • 2
  1. 1.Institute of Heteroorganic Compounds of the Academy of Sciences of the USSRUSSR
  2. 2.Institute of Biochemistry of the Academy of Sciences of the Lithuanian SSRUSSR

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