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Volume # 6(19), November - December 2001 — "Arylation of diethyl malonate with pentafluorobenzenes."

Fluorine Notes, 2001, 19, 5-6

 

ARYLATION OF DIETHYL MALONATE WITH PENTAFLUOROBENZENES.

S. Igumnov, V. Don, A. Gontar

It is known that electron-withdrawing substituents in perfluorinated aromatic compounds activate the para-position of benzene ring to nucleophilic substitution [1].
Perfluorinated aromatic compounds (I) containing electron-withdrawing substituents such as CF3, NO2, CN arylate malonic ester in DMF in the presence of KF with the formation of the corresponding di-esters (II) with - 80% yield.



Heptafluoroxylene was synthesized with good yield from diester (II; X=CF3) by hydrolysis with further decarboxylation. Hexafluoroxylene was used for synthesis of other fluorinated aromatic compounds.



1. W.A. Sheppard, C.M. Sharts . Organic Fluorine Chemistry [ Russian Translation], Mir, Moscow. 1972

 

Fluorine Notes, 2001, 19, 5-6

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