o-carboxybenzoyl- and o-hydroxybenzoylferrocene and their derivatives

Summary

• 1. In a study of the infrared and ultraviolet spectra of o-carboxybenzoylferrocene and some of its derivatives it was shown that both in the crystals and in solutions these substances exist in the open carboxy form and, within the limits of the sensitivity of the spectrographic method, show no signs of the presence of the cyclic phthalide form.

• 2. o-Hydroxybenzoylferrocene was prepared by the condensation of salicyloyl chloride with ferrocene in presence of aluminum chloride. o-Hydroxybenzoylferrocene was converted into various derivatives.

• 3. According to the infrared and ultraviolet spectra, o-hydroxybenzoylferrocene molecules contain an intermolecular chelating hydrogen bond O-H...O.

• 4. The reduction of o-hydroxybenzoylferrocene with lithium aluminum hydride gaveα-o-hydroxyphenylferrocenemethanol, which is extremely readily alkylated.