Related Experiment Video
Updated: Apr 14, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Development and Mechanistic Studies of Oxidative Prins-Semipinacol Cyclization Reactions
Max O Kogut1, Karen R Garn1, Michael J Kerner1
1Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Abstract:
This work shows that allylic alcohols or silyl ethers promote hydride abstraction leading to direct carbon-carbon bond formation or carbon-oxygen bond formation followed by rearrangement, providing the stereoselective construction of spirocyclic ethers through a Prins-semipinacol pathway. A kinetic isotope effect study showed that hydride abstraction is the rate-determining step, consistent with the presence of a distal nucleophilic group lowering the transition state free energy of the oxidation step.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Related Concept Videos
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
Thermal and Photochemical Electrocyclic Reactions: Overview
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...