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

Research output: Contribution to journalArticle

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

Fingerprint

Fluorination
fluorination
Oxides
cleavage
Nitriles
oxides
nitriles
synthesis
cyclohexene
selectfluor

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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 journalArticle

Rajawinslin, RR, Raihan, MJ, Janreddy, D, Kavala, V, Kuo, CW, Kuo, TS, Chen, ML, He, CH & Yao, C-F 2013, 'Selectfluor-mediated fluorination and C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides', European Journal of Organic Chemistry, no. 25, pp. 5743-5749. https://doi.org/10.1002/ejoc.201300599
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. / Selectfluor-mediated fluorination and C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides. In: European Journal of Organic Chemistry. 2013 ; No. 25. pp. 5743-5749.
@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 Ching-Fa Yao",
year = "2013",
month = "9",
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

SP - 5743

EP - 5749

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 25

ER -