title: From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual SNAr via thiolate displacement?
abstract: Treatment of meso 2-ethylhexyl-3-mercaptopropionate substituted porphyrins with base at room temperature generated a porphyrin thiolate anion which in situ reacted in a nucleophilic aromatic substitution (SNAr) reaction with remaining thioether derivative. This reaction yielded S-linked bisporphyrins in good yields, with mechanistic insight obtained via displacement reactions. Additionally, SNAr of the thioether chain was achieved using S- and organolithium nucleophiles.
authors.affiliation: School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St., Dublin 2, Ireland. sengem@tcd.ie.
authors.forename: Aoife A
authors.initials: AA
authors.lastname: Ryan
authors.forename: Shane
authors.initials: S
authors.lastname: Plunkett
authors.forename: Aoife
authors.initials: A
authors.lastname: Casey
authors.forename: Thomas
authors.initials: T
authors.lastname: McCabe
authors.forename: Mathias O
authors.initials: MO
authors.lastname: Senge
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D019281:Dimerization; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
chemical_list: D009942:Organometallic Compounds; D011166:Porphyrins; D013440:Sulfides; D010165:Palladium; D013455:Sulfur