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1 2007

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The Role of Alkali and Alkaline Earth Metal Ions on the Hydrolysis of 2-Ferrocenyl-1,3-dioxane in Acetonitrile Solutions

Navarro E., González F., Astudillo P., Vázquez-Hernández M., Hernández-Rodríguez M., Juaristi E.

Polish Journal of Chemistry

2007

Vol. 81, nr 5-6

921-930

he hydrolysis of 2-ferrocenyl-1,3-dioxane in the presence of different alkali (Li+, Na+, K+ ), alkaline earth (Mg2+, Ca2+ ), and transition metal ions (Zn2+) was studied in acetonitrile solutions. The evolution of the hydrolysis of the dioxane ketalmoiety and the formation of the reaction products was monitored by analysis of the electrochemical oxidation potential of the ferrocenyl redox centre, which maintains its integrity in the reaction and facilitates the determination of the concentrations of both the starting material and products. It was found that only Ca2+ promotes the hydrolysis of 2-ferrocenyl- 1,3-dioxane to produce ferrocenecarboxaldehyde and 1,3-propanediol in up to quantitative yield when an excess of the Ca2+ metal ion is present. Theoretical calculations (B3LYP/3-21G*) led to a proposal for the hydrolysis mechanism, in which coordination of solvated calcium to theO–C–O dioxane segment is determinant for the process to begin.