Conclusions
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1.
Unsubstituted alkanoic acid amides R(CH2)4CONH2 (R=H or alkyl) convert in Na2S2O8-CuCl2 and Na2S2O8-NaCl oxidation systems via intermediate amidyl radicals R(CH2)4C(O)NH intoγ- and δ-lactones with a considerable predominance ofγ-lactones.
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2.
Monoalkyl amides of alkanoic acids are lactonized to an inappreciable extent by the action of the S2O8 2−-Cl− system; N,N-diethyl valeramide undergoes oxidative dealkylation into N-alkyl valeramide.
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3.
As the result of an oxidative, Hoffmann type rearrangement in a Na2S2O8-NaCl-NaOH system, unsubstituted alkanoic acid amides convert into amines containing one carbon atom less than the initial amides.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2751–2757, December, 1982.
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Troyanskii, E.I., Svitan'ko, I.V. & Nikishin, G.I. Reaction of amidyl radicals in sodium peroxydisulfate-metal chloride oxidation systems. Russ Chem Bull 31, 2432–2437 (1982). https://doi.org/10.1007/BF00957713
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DOI: https://doi.org/10.1007/BF00957713