Reactions of (chlorodifluoromethyl)benzene and (chlorodifluoromethoxy)benzene with nucleophilic reagents

Guidotti, Jérôme; Schanen, Vincent; Tordeux, Marc; Wakselman, Claude

doi:10.1016/j.jfluchem.2004.10.001

Cited by 20 publications

(18 citation statements)

References 8 publications

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“…There are only a few reactions designed for constructing compounds containing the difluoro diether (OCF 2 O) group. Aromatic derivatives of this type have been prepared mainly by reacting various reagents with nucleophilic fluorides (e.g., HF, AgF, SbF 3 Bu 4 NH 2 F 3 ) with either dichlorodioxomethylene derivatives or thiocarbonates 88,89. Considerably fewer methods leading to alicyclic or acyclic derivatives could be found 90.…”

Section: Fluorination Reactions With Common Halogen‐free Substratesmentioning

confidence: 99%

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

2009

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Although known for more than a century, bromine trifluoride is not a common reagent in day to day research work in organic chemistry. Its tendency to react exothermically with solvents containing Lewis base elements such as water, acetone or ethers distanced it from the mind of many. Still, under the proper conditions, it can perform quite a few selective reactions which are difficult to achieve by other reagents. We discuss in this review reactions which have been published in the last 30 years. They consist of fluorinating heteroatoms, substituting carbon‐halogen bonds with carbon‐fluorine bonds, syntheses of anesthetics, construction of the trifluoromethyl (CF3) and the difluoromethylene (CF2) groups, aromatic brominations and more.

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Section: Fluorination Reactions With Common Halogen‐free Substratesmentioning

confidence: 99%

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

2009

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“…Aromatic derivatives of this type have been prepared mainly by reacting various reagents with nucleophilic fluorides (e.g., HF, AgF, SbF 3 Bu 4 NH 2 F 3 ) with either dichlorodioxomethylene derivatives or thiocarbonates. [88,89] Considerably fewer methods leading to alicyclic or acyclic derivatives could be found. [90] Here too bromine trifluoride was put to a good use.…”

Section: Forming Trifluoromethyl and Difluoromethyl Ethersmentioning

confidence: 99%

Selective Reactions of Bromine Trifluoride in Organic Chemistry

Rozen

2010

Adv Synth Catal

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Although known for more than a century, bromine trifluoride is not a common reagent in day to day research work in organic chemistry. Its tendency to react exothermically with solvents containing Lewis base elements such as water, acetone or ethers distanced it from the mind of many. Still, under the proper conditions, it can perform quite a few selective reactions which are difficult to achieve by other reagents. We discuss in this review reactions which have been published in the last 30 years. They consist of fluorinating heteroatoms, substituting carbon-halogen bonds with carbon-fluorine bonds, syntheses of anesthetics, construction of the trifluoromethyl (CF 3 ) and the difluoromethylene (CF 2 ) groups, aromatic brominations and more.

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“…Apparently, high temperatures above 150°C are needed to achieve a considerable conversion of the dichloride to the diphenoxide. The reaction temperature in the experiments of Dolbier et al [3] and Guidotti et al [16] was between 100°C and 120°C. Therefore, for thermal laboratory scale preparations, DMPU under reflux for one hour seems to be a good choice of parameters.…”

Section: Introductionmentioning

confidence: 98%

“…The solvent HMPA is known to favour S N 2 reactions and to increase their rate. How exactly the mechanism works is though not clear among all authors of previous related publications [3,16,17]. In microwave reactions and subsequent qNMR studies, the influence of temperature, time and excess molar equivalents of sodium phenolate were compared.…”

Section: Introductionmentioning

confidence: 99%

Improved route to a diphenoxide-based precursor for chemical vapour deposition of parylene AF-4

2021

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In this work, we present the synthesis of an alternative precursor for chemical vapour deposition of parylene AF-4 to the widely used standard, octafluoro[2.2]paracyclophane. The standard precursor suffers from uncertainties in its supply chain and its synthesis is of low yield. A comparison between different reaction parameters and solvents is drawn by means of thermal, laboratory-scale and microwave-assisted reactions and quantitative nuclear magnetic resonance (qNMR) studies.

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Reactions of (chlorodifluoromethyl)benzene and (chlorodifluoromethoxy)benzene with nucleophilic reagents

Cited by 20 publications

References 8 publications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Selective Reactions of Bromine Trifluoride in Organic Chemistry

Improved route to a diphenoxide-based precursor for chemical vapour deposition of parylene AF-4

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