title: A new route to meso-formyl porphyrins.
abstract: Prior syntheses of porphyrins bearing meso-formyl groups have generally employed the Vilsmeier formylation of an acid-resistant copper or nickel porphyrin. A new approach for the synthesis of free base porphyrins bearing one or two (cis or trans) meso-formyl substituents entails the use of a dipyrromethane bearing an acetal group at the 5-position, a dipyrromethane-1-carbinol bearing an acetal group at the 5-position or carbinol position, or a dipyrromethane-1,9-dicarbinol bearing an acetal group at a carbinol position. Treatment of the resulting meso-acetal-substituted free base porphyrin to gentle acidic hydrolysis yields the corresponding meso-formyl porphyrin.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Arumugham
authors.initials: A
authors.lastname: Balakumar
authors.forename: Kannan
authors.initials: K
authors.lastname: Muthukumaran
authors.forename: Jonathan S
authors.initials: JS
authors.lastname: Lindsey
mesh_terms: D003300:Copper / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D011166:Porphyrins; D003300:Copper; D009532:Nickel