Conclusions
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1.
The interaction of O-mesitylenesulfonyl-, O-mesitoyl-, O-(2,4-dinitrophenyl)-, and O-picrylacetoximes with n-butylamine has been investigated. It was shown that it was possible to use only the first two esters for the synthesis of diaziridines based on ketones.
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2.
The use of esters of acetaldoximes in reactions with amines is not promising for the synthesis of diaziridines.
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3.
Nucleophilic substitution of the oxime group by the butylamine group occurred in the reaction of butylamine with O-(2,4-dinitrophenyl)- and O-picryloximes.
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A. N. Mikhailyuk, N. N. Makhova, A. E. Bova, L. I. Khmel'nitskii, and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1566 (1978).
J. Tamura, J. Minamikawa, and M. Ikeda, Synthesis, 1–17 (1977).
Swedish Patent No. 6600834 (1966): Chem. Abs.,66, 28501a (1967).
J. Tamura, J. Minamikawa, K. Sumoto, S. Fujii, and M. J. Ikeda, J. Org. Chem.,38, 1239 (1973).
J. I. Smith and O. W. Cass, J. Am. Chem. Soc.,54, 1603 (1939).
W. N. Marmer and J. Maerker, J. Org. Chem.,37, 3520 (1972).
A. O. Ilvespaa and A. Marxer, Helv. Chim. Acta,46, 2009 (1963).
Van der Kam, Rec. Trav. Chim.,45, 732 (1926).
Handbook of Chemistry [in Russian], Vol. 11, Khimiya, Moscow (1971).
A. A. Dudinskaya, A. E. Bova, L. I. Khmel'nitskii, and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1523 (1971).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2107–2110. September, 1982.
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Makhova, N.N., Petukhova, V.Y. & Khmel'nitskii, L.I. Synthesis of diaziridines from oxime esters. Russ Chem Bull 31, 1858–1862 (1982). https://doi.org/10.1007/BF00952389
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DOI: https://doi.org/10.1007/BF00952389