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

  • E. A. Shapiro
  • T. N. Romanova
  • T. A. Bunkina
  • I. E. Dolgii
  • I. M. Nefedov
Organic Chemistry

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.

     

Keywords

Ester Ethyl Acetylene Diene Carbene 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • E. A. Shapiro
    • 1
  • T. N. Romanova
    • 1
  • T. A. Bunkina
    • 1
  • I. E. Dolgii
    • 1
  • I. M. Nefedov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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