SELECTIVE (N-15) NITRATION OF 2,2-DIPHENYL-1-(2,4-DINITROPHENYL)-HYDRAZINE OR 2,2-DIPHENYL-1-(2,6-DINITROPHENYL)-HYDRAZINE OR 2,2-DIPHENYL-1-(2,4-DINITROPHENYL)-HYDRAZYL OR2,2-DIPHENYL-1-(2,6-DINITROPHENYL)-HYDRAZYL

Treatment of the title compounds with sodium [N-15]nitrite in the pres ence of crown ether 15-crown-5 led to selective nitration yielding 2-( para-[N-15]nitrophenyl)-2-phenyl-1-(2,4- or 2,6-dinitrophenyl) hydrazi nes. When starting from the 2,6-dinitro-derivative under the same reac tion conditions, a di-[N-15]nitro-derivative in the para-phenyl and 4- positions (picryl) was also obtained. The same reaction carried out wi th [N-15]nitrous acid afforded the same products mentioned above and, in addition when using the 2,6-disubstituted compound, a tri-[N-15]nit ro-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.