Vol 3 No 2 (2016)
Articles

Dimethyl Sulphoxide a Useful Reagent for Organic Synthesis

N.D. Zargar
Department of Chemistry University of Kashmir Srinagar, J&K
K.Z. Khan
Department of Chemistry University of Kashmir Srinagar, J&K
Published January 26, 2017
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Keywords
  • Ylide,
  • Methylthiomethylation,
  • Acetoxy coumarins,
  • Polyporic acid,
  • N-bromosuccinimide DMSO,
  • Acetic anhydride.
  • ...More
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Abstract

Dimethyl sulphoxide as a reagent brings about N-methylthiomethylation and N,N/-methyl -thiomethylation in substituted barbituric acids. It converts 4-acetoxy coumarins to corresponding ylides and brings about methylene insertion in 1,6-naphtharidenes at reflux temperature.DMSO activated by trifluoro-aceticanhydride brings about formation of mono, bis and tris-sulphonic substituted derivatives when interacted with cyclo pentadiene and trimethylsilyl cyclopentadiene.This reagent converts 3-Nitro-4-hydroxy coumarins to salicylic acid in dichloromethane at low temperature.DMSO-acetic anhydride reagent converts enols to sulphur ylides, introduces methylthiomethyl group into phenols and oxidizes secondary alcohols to corresponding ketones. It brings about oxidative rearrangement in polyporic acid and converts 4-hydroxy coumarins and its 3-substituted derivatives into a wide range of products under different conditions.DMSO-SO3 pyridine complex in presence of triethyl amine oxidizes cis-diols to corresponding quinones.DMSO-activated by N-bromosuccinimide brings about methylation of alcohols and converts diols to their corresponding methylene-acetals.  

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