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Issue 55, 2019
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Development of a safely handleable synthetic equivalent of cyanonitrile oxide by 1,3-dipolar cycloaddition of nitroacetonitrile

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Abstract

Dianionic cyano-aci-nitroacetate affords 3-cyanoisoxazol(in)es upon heating with a range of dipolarophiles in the presence of hydrochloric acid. In this reaction, nitroacetonitrile is formed as an intermediate active species, which serves as a synthetic equivalent of cyanonitrile oxide that can participate in a 1,3-dipolar cycloaddition reaction.

Graphical abstract: Development of a safely handleable synthetic equivalent of cyanonitrile oxide by 1,3-dipolar cycloaddition of nitroacetonitrile

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Publication details

The article was received on 19 May 2019, accepted on 04 Jun 2019 and first published on 04 Jun 2019


Article type: Communication
DOI: 10.1039/C9CC03875B
Chem. Commun., 2019,55, 7903-7905
  • Open access: Creative Commons BY license
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    Development of a safely handleable synthetic equivalent of cyanonitrile oxide by 1,3-dipolar cycloaddition of nitroacetonitrile

    N. Nishiwaki, Y. Kumegawa, K. Iwai and S. Yokoyama, Chem. Commun., 2019, 55, 7903
    DOI: 10.1039/C9CC03875B

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