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meso-Aryl-3-alkyl-2-oxachlorins.
- Source :
-
Journal of Organic Chemistry . 7/20/2012, Vol. 77 Issue 14, p6199-6207. 9p. - Publication Year :
- 2012
-
Abstract
- The formal replacement of a pyrrole moiety of meso-tetraarylporphyrin 1 by an oxazole moiety is described. The key step is the conversion of porpholactones 4 (prepared by a known two-step oxidation procedure from 1) by addition of alkyl Grignard reagent to form meso-tetraaryl-3-alkyl-2-oxachlorins 9 (alkyloxazolochlorins; alkyl = Me, Et, iPr). Hemiacetal 9 can be converted to an acetal, reduced to an ether, or converted to bis-alkyloxazolochlorins 11. The optical properties (UV-visible and fluorescence spectroscopy) are described. The chlorin-like optical properties of the alkyloxazolochlorins are compared to regular chlorins, such as 2,3-dihydroxychlorins and nonalkylated oxazolochlorins made by reduction from porpholactone 4. The conformations of the mono- and bis-alkylated 2-oxachlorins, as determined by single crystal X-ray diffractometry, are essentially planar, thus proving that their optical properties are largely due to their intrinsic electronic properties and not affected by conformational effects. The mono- and bis-3-alkyl-2-oxachlorins are a class of readily prepared and oxidatively stable chlorins. [ABSTRACT FROM AUTHOR]
- Subjects :
- *PYRROLES
*OXAZOLES
*ACETAL resins
*ETHER (Anesthetic)
*CHLORINS
*X-ray diffraction
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 77
- Issue :
- 14
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 78350282
- Full Text :
- https://doi.org/10.1021/jo300964v