A la recherche des ferrocenylphospholes

Article abstract of DOI:10.1016/0022-328X(87)85133-1

While investigating the synthesis of 1-ferrocenylphospholes, we made three original discoveries. (1), It was possible to couple an aromatic cycle with the dienic system of a phosphole in the presence of AlCl3 provided that the lone pair at phosphorus is blocked by complexation. 2-Arylphospholene complexes are thus obtained. (2), The Friedel-Crafts reaction between an aromatic cycle and a halogenophosphine is greatly favoured by the complexation of phosphorus.This was demonstrated for the condensation of ferrocene and 1-bromo-3,4-dimethylphospholene. (3), The thermolysis of a 1-cyclopentadienylphosphole Fe(CO)4 complex is a new route to phosphaferrocenes.In addition, a 1,1'-bis(phospholyl)ferrocene has been prepared by reaction of a 1-cyclopentadienylphosphole, first with butyllithium, and then with FeCl2.