A New Approach for Ferrocenyl-Cyclopentenone and Ferrocenyl-Cyclopentenedione Compound Synthesis

作者:Li Jie; Ma Jian Ping; Liu Fengling; Wu Xiang Wen; Dong Yu Bin*; Huang Ru Qi
来源:Organometallics, 2008, 27(21): 5446-5452.
DOI:10.1021/om800246s

摘要

A simple and convenient route for the synthesis of the ferrocenyl-cyclopentenone compounds (3 and 7) and ferrocenyl-cyclopentenedione compounds (4 and 8) has been developed. Compounds 3 and 7 were obtained by a selective oxidating reaction of the ferrocenyl-cyclopenta[d]pyridazine species of 2 and 6 in CH,Cl, in air, respectively. Compounds 4 and 8 were generated by a hydrolysis reaction of 3 and 7 in a H(2)O/EtOH mixed solvent system in the presence of SnCl(2), respectively. The substituted ferrocenyl group plays a central role in the formation of the ferrocenyl-cyclopentenone (3 and 7) and ferrocenyl-cyclopentenedione (4 and 8) derivatives, which is demonstrated well by the current experimental data as well as the theoretical calculations. All the new ferrocene-containing complexes have been characterized by elemental analysis, IR spectra, and (1)H NMR spectroscopy, as well as for 3, 4, 5, 7, 8, and 9 by X-ray diffraction analysis. In addition, the luminescent properties of 1-4 were investigated preliminarily in CH,Cl, at room temperature.