Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements: Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins
Regiospecificity of pyrrole subunit OsO4 oxidation in porphyrins is affected significantly by the presence of electron-withdrawing groups on the macrocycle, the oxidation taking place at the subunit in the quadrant opposite to the electronegative group. Migratory aptitudes in subsequent pinacol-pinacolone rearrangements of porphyrin and pheophorbide vic-dihydroxy systems are likewise dependent upon the presence of electron-withdrawing functionalities. © 1992.
Publication Source (Journal or Book title)
Pandey, R., Shiau, F., Isaac, M., Ramaprasad, S., Dougherty, T., & Smith, K. (1992). Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements: Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins. Tetrahedron Letters, 33 (51), 7815-7818. https://doi.org/10.1016/S0040-4039(00)74751-4