Related Experiment Video
Updated: Apr 25, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
C-C Bond Formation between Fischer Carbene Complexes and Allylic Alcohols by a [3,4] Sigmatropic Rearrangement
J Barluenga1, E Rubio, J A López-Pelegrín
1Instituto Universitario de Química Organometálica "Enrique Moles", Unidad Asociada al CSIC, Universidad de Oviedo, Julian Clavería 8, E-33071 Oviedo, Spain, Fax: (+34) 98-510-34-50. barluenga@sauron.quimica.uniovi.es.
Abstract:
A [1,2] M(CO)5 shift promotes a [3,4] sigmatropic rearrangement after the addition of allylic alcohols to Fischer alkenylcarbene complexes of tungsten or chromium in the presence of alkoxide ions. This opens a new synthetic route to the adducts 1. The reaction is also applicable to propargylic alcohols. [M]=Mo(CO)5 , W(CO)5 .
More Related Videos
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Thermal Sigmatropic Reactions: Overview
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
π Molecular Orbitals of the Allyl Cation and Anion