Free base meso-tetraaryl-morpholinochlorins and porpholactone from meso-tetraaryl-2,3-dihydroxy-chlorin

meso-Tetraaryl-2,3-dihydroxychlorins (1) were converted in one step to the novel free base macrocycles meso-tetraaryl-2,3-dialkoxy-2a-oxa-2a-homoporphyrins (morpholinochlorins, 3). Their bathochromically shifted chlorin-type UV-vis spectra indicate the presence of a nonplanar chromophore. The struct...

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Veröffentlicht in:Organic letters 2003-01, Vol.5 (1), p.19-22
Hauptverfasser: McCarthy, Jason R, Jenkins, Hilary A, Brückner, Christian
Format: Artikel
Sprache:eng
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Zusammenfassung:meso-Tetraaryl-2,3-dihydroxychlorins (1) were converted in one step to the novel free base macrocycles meso-tetraaryl-2,3-dialkoxy-2a-oxa-2a-homoporphyrins (morpholinochlorins, 3). Their bathochromically shifted chlorin-type UV-vis spectra indicate the presence of a nonplanar chromophore. The structure of meso-tetratolyldiethoxymorpholinochlorin (3b), as determined by X-ray crystallography, was found to be largely planar, suggesting significant conformational flexibility of these macrocycles. Oxidation of diol 1 with MnO(4)(-) generates known porpholactone 4 in high yields. [reaction--see text]
ISSN:1523-7060
DOI:10.1021/ol027072a