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      https://www.ias.ac.in/article/fulltext/jcsc/133/0006

    • Keywords

       

      Ynamide; hydrochlorination; iodochlorination; enamide; epoxy-ynamide; stereoselective; X-ray structure

    • Abstract

       

      AlCl3 acts as a chlorinating agent for ynamides in the presence of stoichiometric amount of water in the environmentally benign solvent dimethylcarbonate, affording efficient access to (E)-a-chloroenamides via hydrochlorination, with water as a protic source. The role of water in the reaction was proven by deuterium labelling experiment. Epoxy-ynamides undergo iodochlorination in addition to the cleavage of the epoxy ring to afford (E/Z)-a-chloro-b-iodo-enamides. Regio- and stereochemical assignments for the products are based on X-ray crystallographic studies.

    • Graphical Abstract

       

      Chloroenamides are formed regio- and stereo-specifically via hydrochlorination of ynamides with AlCl3+H2O (1:1) in a dimethyl carbonate; aryl substituted epoxy ynamides afford (iodo)(chloro) enamides upon treatment with ICl.

    • Author Affiliations

       

      ALLA SIVA REDDY MANDALA ANITHA SURAJ K C KUMARA SWAMY1

      1. School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India
    • Dates

       
  • Journal of Chemical Sciences | News

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