A new route to meso-formyl porphyrins.
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.
Balakumar
Arumugham
A
Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
Muthukumaran
Kannan
K
Lindsey
Jonathan S
JS
D003300:Copper / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry
D011166:Porphyrins; D003300:Copper; D009532:Nickel