meso-Arylporpholactones and their Reduction Products

• Published in: Journal of organic chemistry Vol. 77; no. 15; pp. 6480 - 6494
• Main Authors: Brückner, Christian, Ogikubo, Junichi, McCarthy, Jason R, Akhigbe, Joshua, Hyland, Michael A, Daddario, Pedro, Worlinsky, Jill L, Zeller, Matthias, Engle, James T, Ziegler, Christopher J, Ranaghan, Matthew J, Sandberg, Megan N, Birge, Robert R
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 03.08.2012; Amer Chemical Soc
• Subjects: Chemical reactivity; Chemistry; Chemistry, Organic; chlorins; Crystallography, X-Ray; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Lactones - chemical synthesis; Lactones - chemistry; Lewis bases; Models, Molecular; moieties; Molecular Structure; optical properties; Organic chemistry; oxazoles; oxidation; Oxidation-Reduction; oxygen; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; PRESSURE-SENSITIVE PAINT; PORPHYRIN CHEMISTRY; PHOTODYNAMIC THERAPY; CORE CONSTRUCTS; ORBITAL THEORY; CHLOROPHYLL ANALOG CHEMISTRY; PHOTOPHYSICAL PROPERTIES; SPARSELY SUBSTITUTED CHLORINS; SYNTHETIC ANALOGS; EXCITED-STATES; MO method; Molecular structure; Nitrogen heterocycle; Molecular interaction; Pyrrole derivatives; Chemical reduction; Steric effect; Optical properties; Chlorins; Oxidation; Chemical reactivity; Chemical synthesis; Oxazole derivatives; Chromophore; Oxygen nitrogen heterocycle; Permanganates; Electronic properties; Theoretical study; Stepwise mechanism; Ketone; X ray diffraction; Planar molecule; Valence; MNDO method; Porphyrin; Oscillator strength; Nucleophilic substitution; Porphyrin derivatives; Conformation; Nucleophile; Crystalline structure

The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4 –-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrr...