Reactivity of the maleimidato ligand in CpFe(CO)2(η1-N-maleimidato) in Diels-Alder reaction with 1,3-diphenylisobenzofuran. The crystal structure of [CpFe(CO)2(η1-N-1,4-diphenyl-1,4-epoxy-1,4-dihydronaphthalene-2,3-dicarboxyimidato)]

Article abstract of DOI:10.1016/S0022-328X(96)06673-9

The title complex reacts with 1,3-diphenylisobenzofuran to afford the Diels-Alder adduct [CpFe(CO)₂(η¹-N-1,4-diphenyl-1,4-epoxy-1,4-dihydronaphthalene-2,3-dicarboxyimidato)] 2 in nearly quantitative yield. The competitive experiment showed that this reaction is around three times slower than the reaction of the parent maleimide with 1,3-diphenylisobenzofuran. The X-ray crystal structure of 2 has been determined. It revealed a scrolled configuration resulting from an endo transition state in Diels-Alder reaction and from various hydrogen bonds and π-π interactions.