TY - JOUR
T1 - The Synthesis and Reactions of Some l-(Nitroaryl)diaziridines
AU - Heine, Harold W.
AU - Williard, Paul G.
AU - Hoye, Thomas R.
PY - 1972/9/1
Y1 - 1972/9/1
N2 - 1-(2,4-Dinitrophenyl)- and l-(2,4,6-trinitrophenyl)diaziridines are prepared by treating appropriate diaziridines with 2,4-dinitrofluorobenzene and 2,4,6-trinitroanisole, respectively. The l-(2,4-dinitrophenyl)-3,3-dialkyl- and l-(2,4,6-trinitrophenyl)-3,3-dialkyldiaziridines are isomerized in refluxing toluene into 2,4-dinitrophenyl- and 2,4,6-trinitrophenylhydrazones. However, l-(2,4-dinitrophenyl)-2,3-dialkyldiaziridines and l-(2,4-dinitrophen)rl)-2,3,3-trialkyldiaziridmes are converted in refluxing toluene into 2-alkyl-6-nitrobenzotriazole 1-oxides and ketones. Acid hydrolysis of the l-(nitroaryl)-2-alkyldiaziridines forms l-nitroaryl-2-alkylhydrazines.
AB - 1-(2,4-Dinitrophenyl)- and l-(2,4,6-trinitrophenyl)diaziridines are prepared by treating appropriate diaziridines with 2,4-dinitrofluorobenzene and 2,4,6-trinitroanisole, respectively. The l-(2,4-dinitrophenyl)-3,3-dialkyl- and l-(2,4,6-trinitrophenyl)-3,3-dialkyldiaziridines are isomerized in refluxing toluene into 2,4-dinitrophenyl- and 2,4,6-trinitrophenylhydrazones. However, l-(2,4-dinitrophenyl)-2,3-dialkyldiaziridines and l-(2,4-dinitrophen)rl)-2,3,3-trialkyldiaziridmes are converted in refluxing toluene into 2-alkyl-6-nitrobenzotriazole 1-oxides and ketones. Acid hydrolysis of the l-(nitroaryl)-2-alkyldiaziridines forms l-nitroaryl-2-alkylhydrazines.
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U2 - 10.1021/jo00984a014
DO - 10.1021/jo00984a014
M3 - Article
AN - SCOPUS:0001607660
SN - 0022-3263
VL - 37
SP - 2980
EP - 2983
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -