title: Preparation of donor-sigma-acceptor molecules using arene-ruthenium chemistry.
abstract: Several donor-sigma acceptor (D-sigma-A) molecules with thioalkyl side chains have been prepared by ruthenium-activated nucleophilic aromatic substition (S(N)Ar) reactions. Selective substitution of chloride from cyclopentadienyl(1,4-dichlorobenzene)ruthenium by using piperazine derivatives as nucleophiles is addressed. This selectivity, in combination with further manipulation of the complexes, allows the preparation of unsymmetrically functionalized tetraalkyl-p-phenylenediamine (TAPD) units which are difficult to synthesize by traditional organic S(N)Ar conditions. Phenanthroline-assisted decomplexation of the product arene-RuCp systems under UV irradiation is described.
authors.affiliation: Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA.
authors.forename: A J
authors.initials: AJ
authors.lastname: Pearson
authors.forename: J J
authors.initials: JJ
authors.lastname: Hwang
mesh_terms: D002614:Chelating Agents / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010879:Piperazines / Q000138:chemical synthesis; D012428:Ruthenium; D013772:Tetramethylphenylenediamine / Q000737:chemistry*; D014466:Ultraviolet Rays
chemical_list: D002614:Chelating Agents; D009942:Organometallic Compounds; D010879:Piperazines; D012428:Ruthenium; D013772:Tetramethylphenylenediamine