Related Experiment Video
Updated: Aug 29, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Synthesis and ring opening reactions of a 2-silabicyclo[2.1.0]pentane
Gerhard Maas1, Birgit Daucher, Alexandra Maier
1Division of Organic Chemistry I, University of Ulm, Albert-Einstein-Allee 11, D-89081 Ulm, Germany. gerhard.maas@chemie.uni-ulm.de
Abstract:
Methyl 2-silabicyclo[2.1.0]pentane-1-carboxylate, obtained by a photochemical intramolecular cyclopropanation reaction of an [small alpha]-allylsilyl-[small alpha]-diazoacetate, undergoes ring opening reactions under different conditions leading to methyl 2-[diisopropyl(methoxy)silylmethyl]cyclopropane-1-carboxylate, a 1-sila-4-cyclopentene-2-carboxylate or an allyl(methoxysilyl)ketene.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Base-Catalyzed Ring-Opening of Epoxides
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
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.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

