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

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

Fingerprint Dive into the research topics of 'Selectfluor-mediated fluorination and C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides'. Together they form a unique fingerprint.

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

@article{c1ed39c273104a2babf8f37007bdc975,

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,

day = "1",

doi = "10.1002/ejoc.201300599",

language = "English",

pages = "5743--5749",

journal = "Annalen der Pharmacie",

issn = "0075-4617",

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 - 2013/9/1

Y1 - 2013/9/1

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

SP - 5743

EP - 5749

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 25

ER -