Rational Synthesis of Meso-Substituted Chlorin Building Blocks
β Scribed by Strachan, Jon-Paul; O'Shea, Donal F.; Balasubramanian, Thiagarajan; Lindsey, Jonathan S.
- Book ID
- 118733794
- Publisher
- American Chemical Society
- Year
- 2000
- Tongue
- English
- Weight
- 160 KB
- Volume
- 65
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
The reaction at room temperature of an aldehyde with excess pyrrole in the absence of solvent affords the meso-substituted dipyrromethane. The reaction is catalyzed with trifluoroacetic acid or with BF9,0(Et)2. The dipyrromethaue is purified by crystallixation or by flash chromatography on silica wi
methyl protecting groups (BBr,, CHCI,) then gave l a in 70 % yield. The 'H and 13C NMR spectra of 1 a (in D,O/ NaOD) and of 1 b (in CDC1,) reflect the symmetry of the molecules. The methoxyl groups are magnetically equivalent in 1 b, but in the open-chain triester precursor 2b, two