Conclusions
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1.
N-nonsubstituted alkanesulfonamides under the action of Na2S2O8-AgNO3-CuSO4 are transformed into 3-oxoalkanesulfonamides by regiospecific γ-oxidation with yields of 90–100% based on consumed substrate.
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2.
The reaction mechanism includes generation of nitrogen-centered sulfonylamidyl radicals and rearrangement with 1,5-hydrogen migration to carbon centered radicals as recorded by EPR. The regiospecificity of the 1,5-hydrogen migration is determined probably by complex formation of the sulfonylamidyl radicals with silver ions.
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Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 7, pp. 1584–1588, July, 1988.
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Troyanskii, É.I., Lazareva, M.I., Zubarev, V.E. et al. Regiospecific oxidation of alkanesulfonamides to 3-oxoalkanesulfonamides. Russ Chem Bull 37, 1401–1405 (1988). https://doi.org/10.1007/BF00962750
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DOI: https://doi.org/10.1007/BF00962750