Selective Synthesis of Vinyl‐ or Alkynyl Chalcogenides from Glycerol and their Water‐Soluble Derivatives

Abstract

Abstract We describe here a convenient procedure to synthesize new vinyl chalcogenides in the reaction of dichalcogenides derived from glycerol with terminal alkynes and NaBH 4 , where polyethylene glycol‐400 (PEG‐400) is the solvent at 30 °C in a N 2 atmosphere. In addition, we report an interesting result for the synthesis of alkynyl chalcogenides using the same substrates with EtOH as the solvent. In both protocols, the corresponding products were obtained in good yields with high selectivity and tolerated a range of terminal alkynes. The treatment of these compounds with acidic cation exchange resin Dowex‐(H + ) produced new water‐soluble organochalcogen compounds.