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

doi:10.1002/ejoc.201300599

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

Department of Chemistry

Research output: Contribution to journal › Article

11 Citations (Scopus)

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 language	English
Pages (from-to)	5743-5749
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.201300599
Publication status	Published - 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

Selectfluor-mediated fluorination and C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides. / Rajawinslin, R. R.; Raihan, Mustafa J.; Janreddy, Donala; Kavala, Veerababurao; Kuo, Chun Wei; Kuo, Ting Shen; Chen, Mei Ling; He, Chiu Hui; Yao, Ching Fa.

In: European Journal of Organic Chemistry, No. 25, 01.09.2013, p. 5743-5749.

Research output: Contribution to journal › Article

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10.1002/ejoc.201300599