Preparation of donor-sigma-acceptor molecules using arene-ruthenium chemistry.
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.
Pearson
A J
AJ
Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA.
Hwang
J J
JJ
D002614:Chelating Agents / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010879:Piperazines / Q000138:chemical synthesis; D012428:Ruthenium; D013772:Tetramethylphenylenediamine / Q000737:chemistry*; D014466:Ultraviolet Rays
D002614:Chelating Agents; D009942:Organometallic Compounds; D010879:Piperazines; D012428:Ruthenium; D013772:Tetramethylphenylenediamine