Prins-Pinacol Rearrangement :

What is Pinacol Pinacolone rearrangement ?

The formation of oxacyclic and carbocyclic ring systems by terminating Prins cyclizations with the pinacol rearrangement in a tandem fashion is known as the Prins-pinacol rearrangement.

it is stereoselective and results in the formation of two C-C bonds, one C-O bond, and two new stereocenters,  protic and Lewis’s acids, nitromethane and dichloromethane solvents are the common in used in the reaction. widely used solvents are nitromethane and dichloromethane alkenyl-substituted cyclic acetals derived from 1,2-diols give rise to highly substituted 3-acyltetrahydrofurans

Prins-Pinacol rearrangement image
Prins-Pinacol rearrangement image,

Mechanism Prins-Pinacol Rearrangement :

The reaction was thought to proceed by an oxonia-Cope rearrangement followed by aldol cyclization, but this hypothesis was rejected based on the observation that enantiomerically enriched acetals gave rise to tetrahydrofuran of high enantiomeric purity and not a racemic mixture as was expected.

mechanism of Prins-Pinacol rearrangement, Prins-Pinacol rearrangement reactions mechanism image
The mechanism Prins-Pinacol rearrangement,

Related Reactions:

  1. pinacol rearrangement


  1. Org. Biomol. Chem., 2014,12, 7257-7260

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