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.

Read more about this topic:  Epoxide

Famous quotes containing the word reactions:

    “In this Journal, my pen is a delicate needle point, tracing out a graph of temperament so as to show its daily fluctuations: grave and gay, up and down, lamentation and revelry, self-love and self-disgust. You get here all my thoughts and opinions, always irresponsible and often contradictory or mutually exclusive, all my moods and vapours, all the varying reactions to environment of this jelly which is I.”
    —W.N.P. Barbellion (1889–1919)

    “Separation anxiety is normal part of development, but individual reactions are partly explained by experience, that is, by how frequently children have been left in the care of others.... A mother who is never apart from her young child may be saying to him or her subliminally: “You are only safe when I’m with you.””
    —Cathy Rindner Tempelsman (20th century)

    “Cuteness in children is totally an adult perspective. The children themselves are unaware that the quality exists, let alone its desirability, until the reactions of grownups inform them.”
    —Leontine Young (20th century)