Conclusions
-
1.
We have studied the synthesis of diaziridines from aldehydes by the reaction of O-mesitylsulfonyl-, O-mesitoyl-,O-(2,4-dinitrophenyl)- and O-picrylhydroxylamines with N-ethylidene-n-butylamine, and with a butylamine-acetaldehyde mixture. For this purpose, only the first two aminating reagents are suitable.
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2.
Two other aminating reagents, viz., O-(2,4-dinitrophenyl)- and O-picrylhydroxylamines, can aminate aldimines at the N atom.
-
3.
The difference in reactivity of the two pairs of aminating reagents is determined by the greater nucleophilic properties of O-mesitylsulfonyl- and O-mesitoylhydroxylamines, as compared with O-(2,4-dinitrophenyl)- and O-picrylhydroxylamines.
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4.
These aminating reagents do not aminate butylamine to butylhydrazine, but are decomposed by its alkalinity to yield the respective acids.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2331–2335, October, 1982.
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Makhova, N.N., Petukhova, V.Y. & Khmel'nitskii, L.I. Reaction of O-substituted hydroxylamines with aldimines and primary aliphatic amines in the synthesis of diaziridines. Russ Chem Bull 31, 2052–2056 (1982). https://doi.org/10.1007/BF00950653
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DOI: https://doi.org/10.1007/BF00950653