An investigation of the chemistry of ferrocenoyl derivatives. The synthesis and reactions of ferrocenoyl imidazolide and its derivatives

Ferrocenoyl imidazolide is synthesized readily from ferrocenecarboxylic acid in one step. It is a red crystalline compound that is stable at <5 °C in the dark and it acts as an efficient ferrocenoyl equivalent. It reacts rapidly with alkoxides to give esters and with thiolates to give thioesters. Its reaction with Lawessonʹs reagent gave diferrocenoyl disulfide. Attempts to make diferrocenoyl peroxide by reacting ferrocenoyl imidazolide with hydrogen peroxide were unsuccessful. Ferrocenoyl imidazolide is converted into triferrocenylmethanol and diferrocenyl ketone in one step by reacting it with ferrocenyl-lithium. The X-ray crystal structures of ferrocenoyl phenyl sulfide and diferrocenoyl disulfide are described.