ISSN:
1588-2780
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
,
Energy, Environment Protection, Nuclear Power Engineering
Notes:
Abstract The present paper reports the regioselective [15NO2]-labeling of N-methoxy-2,4,6-trinitroaniline and 2,2-diphenyl-1-picrylhydrazine (reduced DPPH). Starting from N-methoxy-2,6-dinitroaniline, or N-methoxy-2,4-dinitroaniline, nitration in methylene chloride with solid sodium [15N]nitrite and 15-crown-5-ether afforded N-methoxy-2,6-dinitro-4-[15N]nitroaniline and N-methoxy-2,4-dinitro-6[15N]nitroaniline, respectively. The same compounds could be prepared in higher purity by nitrodecarboxylation (ipso-substitution) under the same conditions starting from N-methoxy-4-carboxy-2,6-dinitroaniline (4-methoxyamino-3,5-dinitrobenzoic acid) and N-methoxy-2-carboxy-4,6-dinitroaniline (2-methoxyamino-3,5-dinitrobenzoic acid). Similarly,ipso-substitution of 2,2-diphenyl-1-(4-carboxy-2,6-dinitrophenyl)-hydrazine afforded, under the same reaction conditions, 2,2-diphenyl-1-(2,6-dinitro-4-[15N]nitrophenyl)-hydrazine. By1H-NMR and13C-NMR it was also observed that under these reaction conditions a14NO2 group can be replaced by a15NO2 group.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF02347393
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