Conclusions
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1.
The azacycloalkanes HNCH2(CH2)nCH2CH2 (n=1–3), on treatment with the Na2S2O8-NaCN-NaOH system, undergo the competing reactions of N-cyanation to give the ureas, C-cyanation to give 2-cyanoazacycloalkanes, and β-fragmentation to give N-cyanomethyl- and N-formylazacycloalkanes. The relative proportions of these three competing reactions depend on the size of the ring.
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2.
Oxidative β-fragmentation of azacycloalkanes also occurs in the K3Fe(CN)6-NaOH and Na2S2O8-AgNO3-NaOH systems.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2537–2546, November, 1985.
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Troyanskii, É.I., Ioffe, V.A. & Nikishin, G.I. Oxidation of azacycloalkanes. Russ Chem Bull 34, 2351–2359 (1985). https://doi.org/10.1007/BF00956799
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DOI: https://doi.org/10.1007/BF00956799