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- W2951112866 abstract "Abstract The title dibromoporphyrins 4 5 and hexabromoporphyrins 11 12 are prepared from H2(2-NO2TPP) 1 and Cu(2-NO2TPP) 8, respectively. The β-nitro group confines the 18-π-annulene system of a tetraphenylporphyrin to its N22H-N24H aromatic delocalization pathway which induces the localization of an antipodal double bond on the porphyrin periphery and enhances its susceptibility to electrophilic attack. Dibromination of H2-NO2TPP) 1 occurs regioselectively affording the 12,13-dibromo-2- nitroporphyrin 2 which, upon Michael addition of NaBH4 and re-aromatization of the resulting nitrochlorin 3, provides an entry to 2,3-dibromoTPP 4 5 as well as an improved route to 2,3- dicyanoporphyrins 6 7 . Perbromination of Cu(2-NO2TPP) 8 and denitration of 9 gave, after demetalation, 2,3,7,8,12,13-hexabromoTPP 12. Both 4 and 12 are structurally characterized by X-ray crystallography." @default.
- W2951112866 created "2019-06-27" @default.
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- W2951112866 date "2010-06-11" @default.
- W2951112866 modified "2023-09-24" @default.
- W2951112866 title "ChemInform Abstract: Regioselective Syntheses and Structural Characterizations of 2,3-Dibromo- and 2,3,7,8,12,13-Hexabromo-5,10,15,20-tetraphenylporphyrins." @default.
- W2951112866 cites W2019969666 @default.
- W2951112866 doi "https://doi.org/10.1002/chin.200005124" @default.
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