Epoxide - Reactions

Reactions

Typical epoxide reactions are listed below.

  • Nucleophilic addition to an epoxide can be base or acid catalyzed.
  • Under acidic conditions, the position the nucleophile attacks is affected both by steric effects (as normally seen for SN2 reactions) and by carbocationic stability (as normally seen for SN1 reactions). Under basic conditions, the nucleophile attacks the least substituted carbon, in accordance with standard SN2 nucleophilic addition reaction process.
  • Hydrolysis of an epoxide in presence of an acid catalyst generates a glycol. The hydrolysis process of epoxides can be considered to be the nucleophilic addition of water to the epoxide under acidic conditions.
  • Reduction of an epoxide with lithium aluminium hydride and water generates an alcohol. This reduction process can be considered to be the nucleophilic addition of hydride (H-) to the epoxide under basic conditions.
  • Reduction with tungsten hexachloride and n-butyllithium generates the alkene. This reaction in effect is a de-epoxidation:
  • Reaction with the NH group in an amine. This covalent bond formation is utilised in epoxy glue with, e.g., Triethylenetetramine (TETA) as a hardener.

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