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Synthesis and garbene decomposition of functionally-substituted diazoacetic esters 4. 2-aminoethyl diazoacetates and N-(2-hydroxyethyl)-N-alkyldiazoacetamides

  • 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.

    Thermocatalytic decomposition of 2-(dialkylamino)ethyl diazoacetates with 2 mole % of an equimolar mixture of Cu and CuSO4 at 110°C, or with 2 mole % of Rh(OAc)2 at 60–100°C, is of the carbene type, and in the presence of dienes and acetylenes affords respectively the cyclopropane- and cyclopropenecarboxylate esters.

  2. 2.

    Facile intramolecular cyclization has been observed in N-(2-hydroxyethyl)-N-alkyl-diazoacetamides to give N-alkylmorpholin-3-ones on treatment with Cu and CuSO4, at 80–110°C.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    E. A. Shapiro, T. N. Romanova, T. A. Bunkina, I. E. Dolgii & I. M. Nefedov

Authors
  1. E. A. Shapiro
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  2. T. N. Romanova
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  3. T. A. Bunkina
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  4. I. E. Dolgii
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  5. I. M. Nefedov
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Additional information

For part 3, see [1].

For a preliminary communication, see [2].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2497–2501, November, 1987.

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Shapiro, E.A., Romanova, T.N., Bunkina, T.A. et al. Synthesis and garbene decomposition of functionally-substituted diazoacetic esters 4. 2-aminoethyl diazoacetates and N-(2-hydroxyethyl)-N-alkyldiazoacetamides. Russ Chem Bull 36, 2318–2321 (1987). https://doi.org/10.1007/BF00957305

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  • DOI: https://doi.org/10.1007/BF00957305

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