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