Conclusions
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1.
Alkanal cyanohydrins (R(CH2)4CH(OH)CN (R=H, alkyl) are transformed into 4- and 5-cyanoalkanoic and alkanolc acids: RCH2CH(CN)CH2CH2COOH, RCH(CN)CH2CH2CH2COOH, and R(CH2)4·COOH, under the effect of peroxydisulfate ions on heating (60–80°C).
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2.
The use of peroxydisulfate instead of the peroxydisulfate-monovalent silver system as the oxidant favors the oxidative rearrangement of the alkanal cyanohydrins into cyanoalkanoic acids due to a decrease in the competitive transformation into alkanoic acids, and also permits obtaining cyanoalkanoic and alkanoic acids with a higher total yield.
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3.
The formation of the cyanohydrin cation-radical and its isomerization with 1,5- and 1,6-migration of the hydrogen atom are the most probable initial stages of the reaction of peroxydisulfates with alkanal cyanohydrins.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2300–2305, October, 1984.
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Ogibin, Y.N., Makhova, I.V., Gorozhankin, S.K. et al. Oxidative rearrangement of alkanal cyanohydrins initiated by peroxydisulfate ions. Russ Chem Bull 33, 2099–2104 (1984). https://doi.org/10.1007/BF00954090
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DOI: https://doi.org/10.1007/BF00954090