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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

15 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 Sept

Keywords

Cleavage reactions
Fluorine
Heterocycles
Ring opening
Synthetic methods

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.201300599

Cite this

@article{aa823ed461bf4259a23443605f700de4,

title = "Selectfluor-mediated fluorination and C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides",

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.",

keywords = "Cleavage reactions, Fluorine, Heterocycles, Ring opening, Synthetic methods",

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

year = "2013",

month = sep,

doi = "10.1002/ejoc.201300599",

language = "English",

pages = "5743--5749",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "25",

}

TY - JOUR

T1 - Selectfluor-mediated fluorination and C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides

AU - Rajawinslin, R. R.

AU - Raihan, Mustafa J.

AU - Janreddy, Donala

AU - Kavala, Veerababurao

AU - Kuo, Chun Wei

AU - Kuo, Ting Shen

AU - Chen, Mei Ling

AU - He, Chiu Hui

AU - Yao, Ching Fa

PY - 2013/9

Y1 - 2013/9

N2 - 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.

AB - 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.

KW - Cleavage reactions

KW - Fluorine

KW - Heterocycles

KW - Ring opening

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84882779153&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84882779153&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201300599

DO - 10.1002/ejoc.201300599

M3 - Article

AN - SCOPUS:84882779153

SN - 1434-193X

SP - 5743

EP - 5749

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 895146: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 895146: Experimental Crystal Structure Determination

Cite this