The nucleophilic substitution of chlorine in derivatives ofβ-chloro-α-methylthioisovaleric acid
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.
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.
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.
KeywordsMethyl Ester Chlorine Methyl Ester Acid Derivative
Unable to display preview. Download preview PDF.
- 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.W. H. Mueller and P. E. Butler, J. Amer. Chem. Soc.,90, 2075 (1968).Google Scholar
- 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.V. A. Zabelaite, Z. A. Stumbrevichute, L. P. Rasteikene, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 2266 (1971).Google Scholar
- 5.L. J. Smith and L. J. Spillane, J. Amer. Chem. Soc.,65, 288 (1943).Google Scholar