Reaction of 2,3,4,5,6-Pentafluorobenzamide with Potassium Hydride: Unexpected Activation of the C–F Bond and Dimerization of Organofluorine Ligand

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Abstract

The reaction of potassium hydride with 2,3,4,5,6-pentafluorobenzamide (FBAm) in dimethoxyethane results in activation of the C–F bond in the para-position to the C(O)NH2 group followed by dimerization of FBAm to form a potassium salt with one free amide group. The structure of the binuclear reaction product {(DME)2K+[C6F5–C(O)N–C6F4–C(O)NH2]–}2 (I) was determined by X-ray diffraction (CCDC 2311402), the purity of the product was confirmed by NMR spectroscopy.

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About the authors

D. S. Yambulatov

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: yambulatov@yandex.ru
Russian Federation, Moscow

T. V. Astaf´eva

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: yambulatov@yandex.ru
Russian Federation, Moscow

J. K. Voronina

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: yambulatov@yandex.ru
Russian Federation, Moscow

S. A. Nikolaevskii

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: sanikol@igic.ras.ru
Russian Federation, Moscow

M. A. Kiskin

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: yambulatov@yandex.ru
Russian Federation, Moscow

I. L. Eremenko

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: yambulatov@yandex.ru
Russian Federation, Moscow

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Supplementary files

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2. Fig. 1. Molecular structures of two independent molecules A (a) and B (b) in complex I (thermal ellipsoids with a probability of 30%, solvate molecules and disordering of DME molecules in molecule A are not shown).

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3. Fig. 2. Fragment of packing I in a crystal (hydrogen atoms in DME molecules and solvate molecules are not shown; dotted lines indicate H-bonds and interactions C=O...π, π...π).

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4. Scheme 1.

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5. Scheme 2.

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