A New Route to Xanthones and Thioxanthones Based on η6-2-Chloro-N,N-Diethylbenzamide-η5-Cyclopentadienyl Iron Hexafluorophosphate

J. Peter Storm; Ruxandra D. Ionescu; David Martinsson; Carl-Magnus Andersson

doi:10.1055/s-2000-6647

Synlett 2000; 2000(7): 0975-0978
DOI: 10.1055/s-2000-6647

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A New Route to Xanthones and Thioxanthones Based on η⁶-2-Chloro-N,N-Diethylbenzamide-η⁵-Cyclopentadienyl Iron Hexafluorophosphate

J. Peter Storm^* , Ruxandra D. Ionescu, David Martinsson, Carl-Magnus Andersson

^*Organic Chemistry 1, Department of Chemistry, Lund University, P.O. Box 124, S-221 00 Lund, Sweden; Fax + 45 43 29 30 30; E-mail: cma@acadia-pharm.com

Abstract

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η⁶-2-Chloro-N,N-diethylbenzamide-η⁵-cyclopentadienyl iron hexafluorophosphate (2) smoothly reacted with phenoxide, thiophenoxide or selenophenoxide, to provide the corresponding heteroatom-bridged biaryl complexes 3a-c. After photolytic decomplexation, directed remote metalation reactions performed on 4a or 4b delivered xanthone or thioxanthone, while the selenoderivative 4c was unreactive under these conditions.

arene complexes - directed remote metalation - heterocycles - iron compounds - nucleophilic aromatic substitutions

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