Abstract
Abstract Free-base meso-propanoyloxylated (–OCOEt) porphyrins and dioxoporphodimethenes (quinoid forms of dihydroxyporphyrins) were efficiently synthesized by the treatment of the corresponding meso-diarylporphyrins with PhI(OAc)2 in propionic acid. Basic hydrolysis of the obtained meso-mono- and -dipropanoyloxyporphyrins provided meso-hydroxyporphyrins (oxophlorins) and dioxoporphodimethenes, respectively. Reduction of the dioxoporphodimethenes generated unstable meso-dihydroxyporphyrins, and one-pot etherification of the meso-dihydroxyporphyrins yielded stable meso-dialkoxyporphyrins.
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