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Reactions of α-oximinoketones with diazomethane

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

Conclusions

  1. 1.

    The direction of diazomethane-induced alkylation ofα-oximinoketones is determined by the structure of the substrate: The presence of a fixed s-cis-carbonyl group leads to N-alkylation in the presence of E-isomeric substrates, and to O-alkylation in the case of Z-isomers; in contrast, the presence of conformationally labile carbonyl groups leads to simultaneous N- and O-alkylation of E-isomeric substrates.

  2. 2.

    Increasing the polarity of the solvent does not significantly affect the direction of diazomethane-induced alkylation of cyclicα-oximinoketones, but leads to a marked increase in the yield of O-alkylation products in the case of conformationally labileα-oximinoketones.

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Authors and Affiliations

  1. F. É. Dzerzhinskii Institute of Chemical Technology, Dnepropetrovsk

    A. V. Prosyanik, Ya. Z. Zorin, A. I. Mishchenko, V. M. Negrimovskii & A. B. Zolotoi

  2. Branch of the Institute of Chemical Physics, Academy of Sciences of the USSR, Chernogolovka

    A. V. Prosyanik, Ya. Z. Zorin, A. I. Mishchenko, V. M. Negrimovskii & A. B. Zolotoi

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  1. A. V. Prosyanik
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  2. Ya. Z. Zorin
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  3. A. I. Mishchenko
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  4. V. M. Negrimovskii
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  5. A. B. Zolotoi
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1840–1847, August, 1985.

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Prosyanik, A.V., Zorin, Y.Z., Mishchenko, A.I. et al. Reactions of α-oximinoketones with diazomethane. Russ Chem Bull 34, 1689–1696 (1985). https://doi.org/10.1007/BF00948518

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  • DOI: https://doi.org/10.1007/BF00948518

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