Epoxidation of Alkenes (mCPBA)
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R2C=CR2 + mCPBA → epoxide + mCBA
Descripción general
Meta-chloroperoxybenzoic acid (mCPBA) converts alkenes to epoxides (oxiranes) in a concerted syn-addition. The peracid oxygen inserts into the C=C bond, forming a strained three-membered ring. Epoxides are highly reactive due to ring strain and serve as versatile synthetic intermediates.
Ejemplo cotidiano
Epoxy resin adhesives (like Araldite) are made from epoxides that cross-link with hardeners to form incredibly strong bonds.
Importancia industrial
El óxido de etileno y el óxido de propileno, los epóxidos más sencillos, se producen a más de 30 millones de toneladas anuales para tensioactivos, poliuretanos y polímeros.
Propiedades
- Tipo
- Organic
- Reversible
- No
- Energía
- Exotérmico
- ΔH
- -200,0 kJ/mol