Selective (15N) nitration of 2,2-diphenyl-1-(2,4- or 2,6-dinitrophenyl)-hydrazines or -hydrazyls

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 41; no. 9; pp. 791 - 799
• Main Authors: Ionita, Petre, Caproiu, Miron T., Luca, Constantin, Constantinescu, Titus, Caldararu, Horia, Balaban, Alexandru T.
• Format: Journal Article
• Language: English
• Published: Chichester John Wiley & Sons, Ltd 01.09.1998; Wiley
• Subjects: 15N-labeling; Biochemical Research Methods; Biochemistry & Molecular Biology; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; crown ether; DPPH; hydrazyl; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Physical Sciences; regioselective nitration; Science & Technology; synthesis; synthesis; N-15-labeling; regioselective nitration; DPPH; crown ether; hydrazyl
• ISSN: 0362-4803; 1099-1344
• DOI: 10.1002/(SICI)1099-1344(1998090)41:9<791::AID-JLCR137>3.0.CO;2-2

Treatment of the title compounds with sodium [15N]nitrite in the presence of crown ether 15‐crown‐5 led to selective nitration yielding 2‐(para‐[15N]nitrophenyl)‐2‐phenyl‐1‐(2,4‐ or 2,6‐dinitrophenyl) hydrazines. When starting from the 2,6‐dinitro‐derivative under the same reaction conditions, a di‐[15N]nitro‐derivative in the para‐phenyl and 4‐positions (picryl) was also obtained. The same reaction carried out with [15N]nitrous acid afforded the same products mentioned above and, in addition when using the 2,6‐disubstituted compound, a tri‐[15N]nitro‐hydrazine in the p,p′, and 4‐positions. The electronic, ESR and NMR spectra of the newly obtained products are presented, and the reaction mechanisms for these unconventional nitrations are discussed. © 1998 John Wiley & Sons, Ltd.