Acyloin rearrangement

What is acyloin rearrangement?

Acyloins are a type of symmetrical α-hydroxy ketones that are analogous to benzoins but with an aliphatic structure.

The naming convention involves adding the suffix “-oin” to the corresponding acid’s stem name.

The acyloin rearrangement is a process whereby an α-hydroxycarbonyl compound is converted into its isomeric form, which is also an α-hydroxycarbonyl compound.

Acyloin rearrangement
Acyloin rearrangement

This rearrangement occurs through the interchange of the carbonyl group and migration of an alkyl group to the adjacent carbon atom. Although this process is typically facilitated by acid or base, it can also occur under pyrolytic conditions. Additionally, the thermal acyloin rearrangement can be accelerated through high pressure.

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