Fries Rearrangement in Synthesis of Ferrocene Derivatives

Goran Eminović; Mirjana D. Vukićević; Zoran Ratković; Danijela Ilić; Rastko D. Vukićević

doi:10.1055/s-2003-42469

LETTER

Fries Rearrangement in Synthesis of Ferrocene Derivatives

Goran Eminović^a, Mirjana D. Vukićević^a, Zoran Ratković^a, Danijela Ilić^b, Rastko D. Vukićević*^a
^a Department of Chemistry, Faculty of Science, University of Kragujevac, R. Domanoviæa 12, P.O. Box 60, 34000 Kragujevac, Serbia and Montenegro
^b Technical Faculty, University of Pritina, 28000 Kosovska Mitrovica, Serbia and Montenegro
Fax: +381(34)335040; e-Mail: vuk49@eunet.yu.;

Abstract

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Abstract

ortho-Ferrocenoylphenol (salicyloylferrocene) has been synthesized and treated with acetyl, propionyl, benzoyl and 2-furoyl chloride to obtain the corresponding (ortho-acyloxybenzoyl)ferrocenes, which were subjected to conditions for the Fries rearrangement. By treatment with AlCl₃ at room temperature in CH₂Cl₂ they afforded the corresponding heteroanular derivatives, 1-acyl-1′-(ortho-hydroxybenzoyl)ferrocenes in good to high yield. Under the same reaction conditions, but in the presence of ferrocene, all keto esters gave the corresponding monoacylferrocenes through an intermolecular Fries rearrangement.

Key words

Fries rearrangement - salicyloylferrocene - (o-acyloxy-benzoyl)ferrocenes - 1-acyl-1′-(o-hydroxybenzoyl)ferrocenes

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References

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