Related Experiment Video
Updated: Jul 11, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
(3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An
Grzegorz Mlostoń1, Katarzyna Urbaniak1, Marcin Palusiak2
1Department of Organic & Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, PL-91-403 Lodz, Poland.
Abstract:
The in situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile smoothly undergo (3+2)-cycloadditions onto the enone fragment of the levoglucosenone molecule, yielding the corresponding, five-membered cycloadducts. In contrast to the 'classic' C(Ph),N(Ph) nitrile imine, reactions with fluorinated C(CF3),N(Ar) analogues lead to stable pyrazolines in a chemo- and stereoselective manner. Based on the result of X-ray single crystal diffraction analysis, their structures were established as exo-cycloadducts with the location of the N-Ar terminus of the 1,3-dipole at the α-position of the enone moiety. The DFT computation demonstrated that the observed reaction pathway results from the strong dominance of kinetic control over thermodynamic control.
More Related Videos
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Cycloaddition Reactions: Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Cycloaddition Reactions: MO Requirements for Photochemical Activation