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Org Lett. 2003 Jan 9;5(1):19-22.

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

Author information

1
Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, USA.

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 MnO(4)(-) generates known porpholactone 4 in high yields. [reaction--see text].

PMID:
12509880
DOI:
10.1021/ol027072a

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