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Synlett 2003(15): 2416-2418  
DOI: 10.1055/s-2003-42469
LETTER
© Georg Thieme Verlag Stuttgart · New York

Fries Rearrangement in Synthesis of Ferrocene Derivatives

Goran Eminovića, Mirjana D. Vukićevića, Zoran Ratkovića, Danijela Ilićb, 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.;
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Publication History

Received 8 September 2003
Publication Date:
07 November 2003 (online)

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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