Isolation of the key intermediates in the catalyst-free conversion of oxiranes to thiiranes in water at ambient temperature

Org Biomol Chem. 2009 Apr 7;7(7):1397-403. doi: 10.1039/b820232j. Epub 2009 Feb 25.

Abstract

Herein we shed light on the mechanism of the reaction of epoxides with ammonium thiocyanate to give the corresponding thiiranes in water, and we present a computational mechanistic model for this highly useful reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Computer Simulation
  • Crystallography, X-Ray
  • Ethylene Oxide / chemistry*
  • Models, Chemical
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry
  • Temperature*
  • Thiocyanates / chemistry
  • Water / chemistry*

Substances

  • Sulfides
  • Thiocyanates
  • Water
  • ethylene sulfide
  • thiocyanic acid
  • Ethylene Oxide