Mono and difluorination of centers α to sulfonates and phosphonates using AcOF

Inna Vints; Julia Gatenyo; Shlomo Rozen

doi:10.1016/j.jfluchem.2013.01.003

Mono and difluorination of centers α to sulfonates and phosphonates using AcOF

Inna Vints, Julia Gatenyo, Shlomo Rozen^*

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

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

14 Scopus citations

Abstract

Acetyl hypofluorite, made easily from diluted fluorine and AcONa is very efficient in fluorinating anionic centers. Compounds containing the moieties CH₂SO₂ or COCH₂PO react with bases to create the corresponding anions which can react with AcOF to produce derivatives containing either the CHFSO₂ or COCHFPO groups. Larger excess of base and AcOF result in the difluoro compounds containing the CF₂SO ₂ or COCF₂PO sub-structures. The fluorinations proceed fast and smoothly and usually with very good yield even when the base is dissolved in aqueous solution as is the case with K₂CO₃ or NaHCO₃.

Original language	English
Pages (from-to)	66-69
Number of pages	4
Journal	Journal of Fluorine Chemistry
Volume	146
DOIs	https://doi.org/10.1016/j.jfluchem.2013.01.003
State	Published - Feb 2013

Keywords

AcOF
Difluoroketophosphonate
Difluorosulfonate
F
Fluoroketophosphonate
Fluorosulfonate

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10.1016/j.jfluchem.2013.01.003

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title = "Mono and difluorination of centers α to sulfonates and phosphonates using AcOF",

abstract = "Acetyl hypofluorite, made easily from diluted fluorine and AcONa is very efficient in fluorinating anionic centers. Compounds containing the moieties CH2SO2 or COCH2PO react with bases to create the corresponding anions which can react with AcOF to produce derivatives containing either the CHFSO2 or COCHFPO groups. Larger excess of base and AcOF result in the difluoro compounds containing the CF2SO 2 or COCF2PO sub-structures. The fluorinations proceed fast and smoothly and usually with very good yield even when the base is dissolved in aqueous solution as is the case with K2CO3 or NaHCO3.",

keywords = "AcOF, Difluoroketophosphonate, Difluorosulfonate, F, Fluoroketophosphonate, Fluorosulfonate",

author = "Inna Vints and Julia Gatenyo and Shlomo Rozen",

year = "2013",

month = feb,

doi = "10.1016/j.jfluchem.2013.01.003",

language = "אנגלית",

volume = "146",

pages = "66--69",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Mono and difluorination of centers α to sulfonates and phosphonates using AcOF

AU - Vints, Inna

AU - Gatenyo, Julia

AU - Rozen, Shlomo

PY - 2013/2

Y1 - 2013/2

N2 - Acetyl hypofluorite, made easily from diluted fluorine and AcONa is very efficient in fluorinating anionic centers. Compounds containing the moieties CH2SO2 or COCH2PO react with bases to create the corresponding anions which can react with AcOF to produce derivatives containing either the CHFSO2 or COCHFPO groups. Larger excess of base and AcOF result in the difluoro compounds containing the CF2SO 2 or COCF2PO sub-structures. The fluorinations proceed fast and smoothly and usually with very good yield even when the base is dissolved in aqueous solution as is the case with K2CO3 or NaHCO3.

AB - Acetyl hypofluorite, made easily from diluted fluorine and AcONa is very efficient in fluorinating anionic centers. Compounds containing the moieties CH2SO2 or COCH2PO react with bases to create the corresponding anions which can react with AcOF to produce derivatives containing either the CHFSO2 or COCHFPO groups. Larger excess of base and AcOF result in the difluoro compounds containing the CF2SO 2 or COCF2PO sub-structures. The fluorinations proceed fast and smoothly and usually with very good yield even when the base is dissolved in aqueous solution as is the case with K2CO3 or NaHCO3.

KW - AcOF

KW - Difluoroketophosphonate

KW - Difluorosulfonate

KW - F

KW - Fluoroketophosphonate

KW - Fluorosulfonate

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DO - 10.1016/j.jfluchem.2013.01.003

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AN - SCOPUS:84873036914

SN - 0022-1139

VL - 146

SP - 66

EP - 69

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

Mono and difluorination of centers α to sulfonates and phosphonates using AcOF

Abstract

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