Constructing the OCF<sub>2</sub>O Moiety Using BrF<sub>3</sub>

Hagooly, Youlia; Rozen, Shlomo

doi:10.1021/jo801116n

Cited by 19 publications

(5 citation statements)

References 29 publications

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“…Asymmetric dialkoxydifluoromethane derivatives were also made and here again with similar behavior toward water. It should be noted, however, that in the case where at least one of the groups attached to the oxygen is aromatic the hydrolytic stability of the CF 2 group is considerably enhanced (Scheme ) 91…”

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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“…5 Recently, we prepared a series of aliphatic difluoromethylene diethers, which were too easily hydrolyzed. 6 We describe here a synthetic method for the preparation of the far more stable aromatic difluoromethylene dioxides from readily available catechols using bromine trifluoride (BrF 3 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of difluoroaryldioxoles using BrF₃

2011

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A novel synthesis of different aromatic and heteroaromatic difluorodioxole derivatives has been developed. The starting materials were catechols, which, after treatment with thiophosgene, formed at 0 °C the respective thiodioxoles. The latter were reacted for a short time with commercially available bromine trifluoride, producing potentially biologically important difluoroaryldioxoles in moderate to high yields.

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“…It should be noted, however, that in the case where at least one of the groups attached to the oxygen is aromatic the hydrolytic stability of the CF 2 group is considerably enhanced (Scheme 33). [91] Scheme 32. The synthesis of aliphatic and aromatic chlorodifluoromethyl ethers.…”

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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Constructing the OCF₂O Moiety Using BrF₃

Cited by 19 publications

References 29 publications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Synthesis of difluoroaryldioxoles using BrF₃

Selective Reactions of Bromine Trifluoride in Organic Chemistry

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Constructing the OCF2O Moiety Using BrF3

Cited by 19 publications

References 29 publications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Synthesis of difluoroaryldioxoles using BrF3

Selective Reactions of Bromine Trifluoride in Organic Chemistry

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Product

Resources

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Constructing the OCF₂O Moiety Using BrF₃

Synthesis of difluoroaryldioxoles using BrF₃