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Novel and improved syntheses of 5,15-diphenylporphyrin and its dipyrrolic precursors

TitleNovel and improved syntheses of 5,15-diphenylporphyrin and its dipyrrolic precursors
Publication TypeJournal Article
Year of Publication1998
AuthorsBruckner, C, Posakony, JJ, Johnson, CK, Boyle, RW, James, BR, Dolphin, D
JournalJournal of Porphyrins and Phthalocyanines
Date PublishedNov-Dec
Type of ArticleArticle
ISBN Number1088-4246
Keywords1, 10-diphenyltripyrrane, 2, 2+2 synthesis, 2-tetrapyrrolylethane, 5, 5-phenyldipyrromethane, ARYLPORPHYRINS, BIPHENYL, CHEMISTRY, COMPLEXES, dipyrromethane, macrocycles, MESO, meso-diphenylporphyrin synthesis, MESOSUBSTITUTED PORPHYRINS, METALLOPORPHYRINS, STEPWISE SYNTHESES, SUBSTITUTED PORPHYRIN

Optimized syntheses of 5,15-diphenylporphyrin (DPP, 1) and its dipynolic precursors are described. A novel procedure for the synthesis of dipyrromethane (2), prepared by hydrodesulfurization of the corresponding di-2-pyrrolylthione (8), is presented, as well as an improved method to isolate large quantities of 5-phenyldipyrromethane (4), prepared by the acid-catalysed condensation of pyrrole with benzaldehyde. These dipyrromethanes are key reagents in two high-yield (2+2)-type syntheses of DPP. 5-Phenyldipyrromethane was formylated to provide 1-formyl- (11) and 1,9-diformyl-5-phenyldipyrromethane (12), and reduction of 11 provided the corresponding hydroxymethyl compound 13, These compounds (11-13), however, were much less efficient precursors to DPP. Two polypyrrolic compounds, 1,1,2,2-dipyrrolylethane (9) and 5,10-diphenyltripyrrane (10), potentially useful for the synthesis of porphyrinic macrocycles, were isolated as side-products during the dipyrromethane and 5-phenyldipyrromethane syntheses. (C) 1998 John Wiley & Sons, Ltd.

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