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• W2019969666 abstract "The title dibromoporphyrins 45 and hexabromoporphyrins 1112 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 45 as well as an improved route to 2,3- dicyanoporphyrins 67. 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.
• W2019969666 created "2016-06-24" @default.
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• W2019969666 date "1999-11-01" @default.
• W2019969666 modified "2023-10-03" @default.
• W2019969666 title "Regioselective syntheses and structural characterizations of 2,3-dibromo-and 2,3,7,8,12,13-hexabromo-5,10,15,20-tetraphenylporphyrins" @default.
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• W2019969666 doi "https://doi.org/10.1016/s0040-4020(99)00811-x" @default.
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