Collect. Czech. Chem. Commun. 1999, 64, 99-106
https://doi.org/10.1135/cccc19990099

Acetylation and Formylation of 3-Ferrocenylpyrroles

Battsengel Gotova,*, Štefan Tomaa and Eva Solčániováb

a Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovak Republic
b Institute of Chemistry, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovak Republic

Abstract

Acetylations of 3-ferrocenyl-1-methylpyrrole as well as 3-cyano-4-ferrocenylpyrrole and 3-cyano-4-ferrocenyl-1-methylpyrrole were performed. The course of the acylation is highly dependent on the acylation agent, that is acetyl chloride/aluminum chloride (method A), trifluoroacetic anhydride-acetic acid mixture (method B) or acetic anhydride/Sc(OTf)3 (method C). Method A gives the acetylation on ferrocene moiety, method B affords the trifluoroacetylation on pyrrole moiety and method C affords pyrrole moiety acetylation. Vielsmeier-Haack formylation gives the products of substitution on pyrrole moiety.

Keywords: Metallocenes; Ferrocenes; Pyrroles; Electrophilic aromatic substitution; Acylation; Formylation.