An improved synthesis of meso-tetraanthrylporphyrin by a kinetically controlled Lindsey reaction

Abstract

Meso-tetraanthrylporphyrin was successfully synthesized in 3.0% yield by a kinetically controlled Lindsey method in which tetraanthrylporphyrinogen was oxidized to meso-tetraanthrylporphyrin only 1 min after the condensation of pyrrole and 9-anthraldehyde had been initiated by the addition of an acid catalyst. A longer condensation time lowered the yield of meso-tetraanthrylporphyrin and made separation and purification more difficult. The electronic spectra are also reported.