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DOI: 10.1055/s-0029-1217012
N-Substitution Reactions of 20-π-Electron β-Tetrakis(trifluoromethyl)-meso-tetraphenylporphyrin
Publikationsverlauf
Publikationsdatum:
23. September 2009 (online)
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Abstract
The N-substitution reactions of 20-π-electron β-tetrakis(trifluoromethyl)-meso-tetraphenylporphyrin 2 with α,ω-dibromoalkanes in N,N-dimethylformamide at room temperature in the presence of various bases gave a variety of N-substituted isophlorins, the nature of which depended on the chain length of α,ω-dibromoalkanes and the reaction conditions. When 1,4-dibromobutane was used, a fascinating N,N′-bridged isophlorin 14 was obtained. In the case of 1,3-dibromopropane or 1,5-dibromopentane, N-monoalkylated or N,N′-dialkylated isophlorins were produced under similar conditions. The reactions of these N-alkylated isophlorins with activated zinc powder were complicated and reduction, hydrolysis, elimination, and intramolecular cyclization were all observed.
Key words
isophlorin - substitutions - porphyrins - cyclizations
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