On the [2,3] sigmatropic rearrangement of allylic nitro compounds
Celia Alameda-Angulo1, Béatrice Quiclet-Sire, Elmar Schmidt
1Laboratoire de Synthèse Organique Associé au CNRS, Ecole Polytechnique, 91128 Palaiseau Cedex, France.
Abstract:
Allylic nitro compounds undergo relatively clean [2,3] sigmatropic rearrangement upon heating in refluxing 1,2-dichlorobenzene in the presence of DABCO to give the corresponding allylic alcohols via the intermediate allylic nitrite. [reaction: see text]
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Related Concept Videos
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope 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 1,5-hexadiene, referred to as...
π Molecular Orbitals of the Allyl Cation and Anion
π Molecular Orbitals of the Allyl Radical
The allyl systems have identical molecular orbitals but differ in the number of π electrons.
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
