Selectfluor-mediated fluorination and C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides

R. R. Rajawinslin, Mustafa J. Raihan, Donala Janreddy, Veerababurao Kavala, Chun Wei Kuo, Ting Shen Kuo, Mei Ling Chen, Chiu Hui He, Ching Fa Yao

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Abstract

A rapid method for the synthesis of long-chain fluorinated compounds using a C-C bond-cleavage reaction was developed. Selectfluor was the most effective fluorinating agent of those tested in this study. Long-chain fluoro dioxo nitriles were formed from isoxazoline N-oxides via nitroso intermediates. A Selectfluor-mediated protocol for the synthesis of long-chain fluorinated compounds from cyclohexene-fused isoxazoline N-oxides by using a C-C bond-cleavage reaction is presented.

Original languageEnglish
Pages (from-to)5743-5749
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
Publication statusPublished - 2013 Sep 1

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Keywords

  • Cleavage reactions
  • Fluorine
  • Heterocycles
  • Ring opening
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rajawinslin, R. R., Raihan, M. J., Janreddy, D., Kavala, V., Kuo, C. W., Kuo, T. S., Chen, M. L., He, C. H., & Yao, C. F. (2013). Selectfluor-mediated fluorination and C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides. European Journal of Organic Chemistry, (25), 5743-5749. https://doi.org/10.1002/ejoc.201300599