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- Title
(3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An Experimental and Computational Study †.
- Authors
Mlostoń, Grzegorz; Urbaniak, Katarzyna; Palusiak, Marcin; Witczak, Zbigniew J.; Würthwein, Ernst-Ulrich
- 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.
- Subjects
NITRILIMINES; THERMODYNAMIC control; KINETIC control; SINGLE crystals
- Publication
Molecules, 2023, Vol 28, Issue 21, p7348
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28217348