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Oxidative rearrangement of cycloalkanone cyanhydrins: efficiency of various oxidants and oxidant systems

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Oxidative rearrangement of cycloalkanone cyanhydrins is most efficiently initiated by Ce(IV) ammonium nitrate and the S2O 2−8 /Ag(I) and S2O 2−8 /Ce(III) oxidant systems. Here the cyclopentanone and cyclohexanone cyanhydrins are converted to 5- and 6-cyanoalkanoic acids, while cycloheptanone cyanhydrin is converted to 4-cyanocycloheptanone.

  2. 2.

    Rearrangement of cycloheptanone cyanhydrin to 4-cyanocycloheptanone also proceeds efficiently by the action of peroxydisulfate ion in the absence of silver and cerium ions.

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Literature cited

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1361–1364, June, 1986.

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Ogibin, Y.N., Gorozhankin, S.K. & Nikishin, G.I. Oxidative rearrangement of cycloalkanone cyanhydrins: efficiency of various oxidants and oxidant systems. Russ Chem Bull 35, 1235–1238 (1986). https://doi.org/10.1007/BF00956605

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  • DOI: https://doi.org/10.1007/BF00956605

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