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 S_N2 reactions) and by carbocationic stability (as normally seen for S_N1 reactions). Under basic conditions, the nucleophile attacks the least substituted carbon, in accordance with standard S_N2 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.