Free Basemeso-Tetraaryl-morpholinochlorins and Porpholactone frommeso-Tetraaryl-2,3-dihydroxy-chlorin
- 11 December 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (1) , 19-22
- https://doi.org/10.1021/ol027072a
Abstract
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 MnO4- generates known porpholactone 4 in high yields.Keywords
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