Chemistry in hydrogen fluoride. 7. A novel synthesis of aryl trifluoromethyl ethers

Feiring, Andrew E.

doi:10.1021/jo01330a017

Cited by 125 publications

(42 citation statements)

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“…1 The other derivatives were synthesized in a similar way, and commercially available reagents and solvents were used unless otherwise noted. Trifluoromethoxyaniline 8) for the synthesis of compound 21 and monoacetylethylenediamine derivative 9) for the synthesis of compound 24 were prepared according to methods described previously.…”

Section: -(11-dimethyl-2-methylthioethylimino)-4-iodo-3h-isobenzofumentioning

confidence: 99%

Flubendiamide, a Novel Insecticide Highly Active against Lepidopterous Insect Pests

et al. 2005

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Flubendiamide, N2 -[1,1-dimethyl-2-(methylsulfonyl)ethyl]-3-iodo-N 1 -[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide, is a novel class of insecticide having a unique chemical structure. The uniqueness of the structure results from three parts with novel substituents; a heptafluoroisopropyl group in the anilide moiety, a sulfonylalkyl group in the aliphatic amide moiety, and an iodine atom at the 3-position of the phthalic acid moiety. The compound shows extremely strong insecticidal activity especially against lepidopterous pests including resistant strains. Flubendiamide would have a novel mode of action, because the insecticidal symptoms accompanied by a discriminative contraction of the larval body are distinguished from those of commercial insecticides. It is also very safe for non-target organisms. Flubendiamide is expected to be a suitable agent for controlling lepidopterous insects as part of the insect resistance management and the integrated pest management programs.

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Section: -(11-dimethyl-2-methylthioethylimino)-4-iodo-3h-isobenzofumentioning

confidence: 99%

Flubendiamide, a Novel Insecticide Highly Active against Lepidopterous Insect Pests

et al. 2005

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“…[74] There are several methods for the preparation of these compounds using reagents such as SF 4 [75] or CCl 4 /HF. [76] Not much is known, however, on aliphatic trifluoromethyl ethers since it was not simple to prepare them. [77] Bromine trifluoride found an important role on this subject using once again the sulfur atom as preliminary anchor for the reagent.…”

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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“…CF 3 lability under HF/Lewis acid conditions was not anticipated while choosing CF 3 O-Ph as an auxiliary solvent as CF 3 O-Ph had been reported to be stable to Friedel-Crafts alkylation (in the presence of BF 3 as Lewis acid) [8][9][10] and was most certainly synthesized with HF and often, Lewis acid catalysts [11][12][13][14][15][16]! A closer look at the literature on the synthesis of trifluoromethoxybenzenes disclosed some interesting points.…”

Section: Precedent For P-rosolic Acid (2) Formationmentioning

confidence: 99%

Lability of the trifluoromethyl group of trifluoromethoxybenzenes under HF/Lewis acid conditions

Belter

2010

Journal of Fluorine Chemistry

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Chemistry in hydrogen fluoride. 7. A novel synthesis of aryl trifluoromethyl ethers

Cited by 125 publications

References 0 publications

Flubendiamide, a Novel Insecticide Highly Active against Lepidopterous Insect Pests

Flubendiamide, a Novel Insecticide Highly Active against Lepidopterous Insect Pests

Selective Reactions of Bromine Trifluoride in Organic Chemistry

Lability of the trifluoromethyl group of trifluoromethoxybenzenes under HF/Lewis acid conditions

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