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Synthesis 2005(8): 1350-1358  
DOI: 10.1055/s-2005-865286
PAPER
© Georg Thieme Verlag Stuttgart · New York

Acylurea Pyrolysis - Thermolysis of N,N′-Disubstituted Ferrocenoylureas as a New Way to N-Monosubstituted Ferrocenecarboxamides

Bernd Schetter*
Humboldt-Universität zu Berlin, Institut für Chemie, Unter den Linden 6, 10099 Berlin, Germany
e-Mail: bernd.schetter@chemie.hu-berlin.de;
Further Information

Publication History

Received 2 November 2004
Publication Date:
07 April 2005 (online)

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Abstract

Several N-monosubstituted amides of ferrocenecarbox­ylic acid were synthesized by pyrolysis of N,N′-disubstituted ferrocenoylureas in boiling dioxane under neutral conditions. The reaction time and the yield were found to be dependent on the nature of the substituents. For the species D1 and D4 a single crystal structure analysis was made. The structural effect of the twist between the amide plane and the cyclopentadienyl rings was investigated.

Keywords

acylurea - pyrolysis - ferrocene - urea - amide - peptide bond - DCC

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36

A scale-up was tried for the synthesis of C1. The reaction was carried out with A1 (2 g) in refluxing dioxane (50 mL). No decrease of the yield was detectable and unconverted A1 could be easily recovered. The yield was 63%.