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Note | Regular issue | Vol 65, No. 12, 2005, pp.3001-3006
Published online, 14th October, 2005
DOI: 10.3987/COM-05-10555
Regiospecific Aryl Nitration of meso-Tetraarylporphyrins: The Directive Effect of para-Substituent

Hong-Liang Zhang, Wei-Min Shi, and Jian Wu*

*Department of Chemistry, Zhejiang University , Hangzhou, 310027, China


Regiospecific nitration of single p-substituted tetraphenylporphyrins with excess nitric acid is reported. The directive effects of different p-substituents, including nitro, acetamido and hydroxy groups, were demonstrated. The electron- withdrawing p-nitro group was found to lead to predominant nitration at the neighboring phenyl ring, and the electron-releasing p-acetamido and p-hydroxy groups lead to adjacent nitration at the same phenyl ring.