Chlorocyclization of Alkenoic Thioester

Chem Pharm Bull (Tokyo). 2024;72(11):1034-1037. doi: 10.1248/cpb.c24-00632.

Abstract

This study introduces a novel method for ring-closing chlorosulfenylation of alkenoic thioesters using N-chlorosuccinimide in hexafluoroisopropanol under mild conditions. This reaction efficiently forms five-membered cyclic sulfur compounds with high selectivity, representing a significant advancement in the synthesis of chlorinated S-heterocycles. Computational analysis using density functional theory demonstrates the superiority of thioester nucleophiles over traditional benzyl sulfides in this reaction, highlighting the energetic preference for thioesters.

Keywords: chlorocyclizaion; density functional theory; heterocycle; hexafluoroisopropanol; sulfenylation.

MeSH terms

  • Alkenes / chemical synthesis
  • Alkenes / chemistry
  • Cyclization
  • Density Functional Theory
  • Esters* / chemical synthesis
  • Esters* / chemistry
  • Molecular Structure
  • Sulfhydryl Compounds / chemical synthesis
  • Sulfhydryl Compounds / chemistry

Substances

  • Esters
  • Sulfhydryl Compounds
  • Alkenes