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EXPERIMENTAL AND COMPUTATIONAL STUDY OF THE REACTION BETWEEN FERROCENYL LITHIUM AND N-PHENYL PHTHALIMIDE

In order to investigate the electronic and structural interactions between organometallic functionalities and heterocycles, [1, 2] a reaction between ferrocenyl lithium (FcLi) and N-phenyl phthalimide (1) was performed. During the course of this reaction an unusual reactivity was observed. The conversion of one equivalent of FcLi with 1, resulted in mono-ferrocenyl lactam 2, which rapidly undergoes ring-chain tautomerism 2  3. When two equivalents of FcLi were used, a bis-ferrocenyl lactone 4, involving a five-membered oxygen bridged heterocycle, was formed. In addition, a tricyclic product 5, in which one of the ferrocene moieties displays a planar chiral substitution pattern, was isolated. The compounds 2 – 5 were characterized spectroscopically and electrochemically. The molecular structures in solid state were defined by X-ray diffraction analysis. The involved reaction mechanisms were explored by use of modern density functional techniques.

ferrocene, ftalidimide, DFT

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