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Intramolecular acid-catalyzed reactions of o-carbomethoxy-ω-diazoacetophenones

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

Conclusions

  1. 1.

    A variety of new o-carbomethoxy-ω-diazoacetophenones and isochromane-1,4-diones were synthesized.

  2. 2.

    The decomposition of o-carbomethoxy-ω-diazoacetophenones in methanol-H2SO4, in constrast to reactions of their o-unsubstituted analogs, takes place via the A-SE2 mechanism. The intramolecular nucleophilic assistance of the o-CO2CH3 group increases the decomposition rate of ω-diazoacetophenones by 13–25 times.

  3. 3.

    A correlation was observed between the acid-catalyzed reaction rates of o-carbomethoxy-ω-diazoacetophenones and Hammet's σ constants for benzene ring substituents.

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Authors and Affiliations

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

    S. V. Chapyshev, L. I. Kurkovskii & V. G. Kartsev

Authors
  1. S. V. Chapyshev
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  2. L. I. Kurkovskii
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  3. V. G. Kartsev
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 837–842, April, 1987.

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Chapyshev, S.V., Kurkovskii, L.I. & Kartsev, V.G. Intramolecular acid-catalyzed reactions of o-carbomethoxy-ω-diazoacetophenones. Russ Chem Bull 36, 765–770 (1987). https://doi.org/10.1007/BF00962316

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  • DOI: https://doi.org/10.1007/BF00962316

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