N-Substitution Reactions of
20-π-Electron β-Tetrakis(trifluoromethyl)-meso-tetraphenylporphyrin

Xiao-Guang Chen; Chao Liu; Dong-Mei Shen; Qing-Yun Chen

doi:10.1055/s-0029-1217012

PAPER

N-Substitution Reactions of 20-π-Electron β-Tetrakis(trifluoromethyl)-meso-tetraphenylporphyrin

Xiao-Guang Chen, Chao Liu, Dong-Mei Shen, Qing-Yun Chen*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, 200032 Shanghai, P. R. of China
Fax: +86(21)64166128; e-Mail: chenqy@mail.sioc.ac.cn;

Abstract

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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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References

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