Oxidation of meso-tetraphenyl-2,3-dihydroxychlorin: simplified synthesis of β,β′-dioxochlorins

DDQ Oxidation of meso-tetraphenyl-cis-2,3-dihydroxychlorins leads to an efficient synthesis of the corresponding 2,3-dioxochlorins. This alternative synthesis of these known chromophores is simple and likely to be more general as compared to established syntheses. A single crystal structure of [meso-tetraphenyl-cis-2,3-dihydroxychlorinato]Ni(II) proves the ruffled structure of the chromophore. The reduction of the free base dioxochlorin allows the preparation of the meso-tetraphenyl-trans-2,3-dihydroxychlorin.