التفاصيل البيبلوغرافية
| العنوان: |
(3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An Experimental and Computational Study †. |
| المؤلفون: |
Mlostoń, Grzegorz, Urbaniak, Katarzyna, Palusiak, Marcin, Witczak, Zbigniew J., Würthwein, Ernst-Ulrich |
| المصدر: |
Molecules; Nov2023, Vol. 28 Issue 21, p7348, 15p |
| مصطلحات موضوعية: |
NITRILIMINES, THERMODYNAMIC control, KINETIC control, SINGLE crystals |
| مستخلص: |
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. [ABSTRACT FROM AUTHOR] |
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