Regioselective Nitration of 5-Phenyl-2,3,7,8,12,18-hexamethyl-13,17-diethylporphine

Alexey Lyubimtsev,^@ Sergey Syrbu, Natal’ya Zheglova, Alexandr Semeikin, and Oscar Koifman

Ivanovo State University of Chemistry and Technology, Ivanovo 153000, Russia

^@Corresponding author E-mail: alexlyubimtsev@mail.ru

Macroheterocycles 2011 4(4) 265-269

DOI: 10.6060/mhc2011.4.05

Received 21.08.2011
Accepted 13.10.2011

Nitration system NaNO2-TFA for regioselective nitration of the meso-positions of 5-phenyl-2,3,7,8,12,18-hexamethyl-
13,17-diethylporphine (1) was examined. The degree of nitration is easily controlled by the amount of NaNO2 used and
by the reaction time. All compounds are characterized by MS, UV-Vis-, and 1H NMR-spectroscopy as well as massspectrometry.

Protonation of transannular protons of some synthesized porphyrins is discussed.

Keywords: Porphyrin, nitration, meso-nitroporphyrins, trifluoroacetic acid, sodium nitrite.

MHC2011_t04n04_265-269.pdf (702.35 KB)

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