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41.3.4.1.1.2 Variation 2: Using Dinitrogen Pentoxide or Dinitrogen Tetroxide

DOI: 10.1055/sos-SD-041-00393

Jahn, U.Science of Synthesis, (201041403.

A variety of secondary amines 73 are nitrated directly by dinitrogen pentoxide in moderate to high yields to give the corresponding nitroamines 74 (Scheme 32).[‌267‌,‌268‌] The dinitrogen pentoxide must be anhydrous to avoid side reactions and the addition temperature should be low. Since the reaction conditions are more neutral, sensitive cyclic structures such as azetidine [73, R1,R2=(CH2)3][‌269‌] or 6-alkyl-1,3,5-triazabicyclo[3.1.0]hexanes[‌270‌] can be nitrated to give the corresponding N-nitroamines. However, formaldehyde aminals (N,N,N,N-tetraalkylmethanediamines) react with cleavage of the aminal to afford N,N-dialkyl-N-nitroamines in 2554% yield.[‌271‌] Pyrimidine is nitrated by dinitrogen pentoxide in the presence of alcohols to give 2,4-dialkoxy-1,3-dinitro-1,2,3,4-tetrahydropyrimidines in 5894% yield.[‌272‌] There is one example of a nitration of diethylamine with dinitrogen tetroxide at 80°C, which gives N,N-diethyl-N-nitroamine in 93% yield.[‌273‌]

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