Jump to main content
Jump to site search

Issue 47, 2018
Previous Article Next Article

Hydroximoyl fluorides as the precursors of nitrile oxides: synthesis, stability and [3 + 2]-cycloaddition with alkynes

Author affiliations

Abstract

The transformation of hydroximoyl fluorides to nitrile oxides for [3 + 2]-cycloaddition with alkynes has been achieved for the first time. The hydroximoyl fluorides used in this work appeared to be not stable, which was proved by a series of experiments. A DFT calculation was performed to better understand the properties of hydroximoyl fluorides. Although not stable, the hydroximoyl fluorides could be successfully converted to the corresponding nitrile oxides for in situ [3 + 2]-cycloaddition with alkynes to yield the isoxazoles. Furthermore, it was feasible to conduct [3 + 2]-cycloaddition reaction without purification after the synthesis of hydroximoyl fluorides from gem-difluoroalkenes. By investigating a class of interesting yet previously rarely explored fluorinated compounds, this work sheds new light on the stability and reactivity of a C–F bond on a C[double bond, length as m-dash]N double bond.

Graphical abstract: Hydroximoyl fluorides as the precursors of nitrile oxides: synthesis, stability and [3 + 2]-cycloaddition with alkynes

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Nov 2018, accepted on 14 Nov 2018 and first published on 15 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02721H
Citation: Org. Biomol. Chem., 2018,16, 9211-9217
  •   Request permissions

    Hydroximoyl fluorides as the precursors of nitrile oxides: synthesis, stability and [3 + 2]-cycloaddition with alkynes

    F. Gao, Z. Fang, R. Su, P. Rui and X. Hu, Org. Biomol. Chem., 2018, 16, 9211
    DOI: 10.1039/C8OB02721H

Search articles by author

Spotlight

Advertisements