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    • Fulltext

       

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/093/04/0593-0600

    • Keywords

       

      Tautomerism; solvolysis; acid chlorides

    • Abstract

       

      Solvolysis of nine representative half ester acid chlorides in aqueous acetone have been studied. Isomers solvolyse at distinctly different rates and furnish the original acids. Contrary to the well accepted views, no evidence for tautomerism or isomerism between the isomeric pairs of acid chlorides could be detected. In a number of cases alkoxy group participates in the solvolysis of neighbouring acid chlorides. This results in (a) rate enhancement and (b) partial or total shift of the reaction pattern from SN2 to SN1. Isomeric half ester acid chlorides, in the presence of a sufficiently strong Lewis acid, could give the same oxonium salt. Rearrangements observed in the reactions of unsymmetrical 1,2- and 1,3-dicarboxylic acid derivatives could be ascribed to the prior formation of common oxonium salt intermediates in the presence of Lewis acids.

    • Author Affiliations

       

      M Vivekananda Bhatt1 Vishwanatha Somayaji1 M Vishnumurthi Rao1

      1. Department of Organic Chemistry, Indian Institute of Science, Bangalore - 560 012, India

    • Dates

       
      Published
      May 1984

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