Issue 14, 1973

Photochemistry of ferrocenyl ketones and acids in dimethyl sulphoxide and related solvents

Abstract

Compounds of the type FcCOAr, FcCOR (R = Alkyl), and FcCHO undergo photoaquation (λ > 280 nm) in wet dimethyl sulphoxide, pyridine, dimethylformamide, and related solvents to give a cyclopentadienyliron salt of the acid ArCO2H or RCO2H together with a molecule of free cyclopentadiene derived from the originally substituted ring. At shorter wavelengths in DMSO a secondary reaction gives rise to the intense purple colouration described previously. Ferrocenecarboxylic acid undergoes similar consecutive changes in these solvents yielding initially a carboxylate and free cyclopentadiene, but then CO2 and a new carboxylate from which starting material could be recovered in 48% yield. With shorter wavelength light a purple colouration developed. The esters of this acid were also found to be photosensitive but subject to strong autoretardation.

Article information

Article type
Paper

J. Chem. Soc., Dalton Trans., 1973, 1468-1475

Photochemistry of ferrocenyl ketones and acids in dimethyl sulphoxide and related solvents

L. H. Ali, A. Cox and T. J. Kemp, J. Chem. Soc., Dalton Trans., 1973, 1468 DOI: 10.1039/DT9730001468

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