Reactions of bromotrifluoromethane and related halides. 8. Condensations with dithionite and hydroxymethanesulfinate salts

Tordeux, Marc; Langlois, Bernard R.; Wakselman, Claude

doi:10.1021/jo00271a041

Cited by 126 publications

(35 citation statements)

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“…1 N a C F 3 Br [20,21] low 44 2 N a C F 3 CO 2 Na [22] high 72 3 Na commercial fair [c] 60 4 K C F 3 SO 2 Cl [23] low 34 5 K C F 3 CO 2 K [22] high 70 6 K C F 3 SiMe 3 [24] high 66 7 C s C F 3 SiMe 3 [25] high 70…”

Section: Purity Of the Reagentsmentioning

confidence: 99%

Benchmark and Solvent‐Free Preparation of Sulfonium Salt Based Electrophilic Trifluoromethylating Reagents

et al. 2009

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Here we describe work devoted to the one‐pot preparation of electrophilic trifluoromethylating reagents. The first part describes a reappraisal of our earlier experimental conditions and leads to an improved protocol that avoids the use of solvent and allows better yields. The second part carefully studies the behavior of biaryl substrates, whose structures can drive the reaction through the formation of original noncyclic or tricyclic dibenzothiophenium salts. New compounds were tested, in a standard reaction with aniline, for their trifluoromethylating power and revealed equivalent or improved reactivity relative to that of existing reagents. Furthermore, contrary to common knowledge, the presence of electron‐donating methyl groups gave reagents with very high activity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Purity Of the Reagentsmentioning

confidence: 99%

Benchmark and Solvent‐Free Preparation of Sulfonium Salt Based Electrophilic Trifluoromethylating Reagents

et al. 2009

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“…GC analysis of the crude residue, with an internal standard, indicated the formation of 9a in a 75% crude yield. 1 …”

Section: Reaction Of Ethyl 3-(phenylsulfonylthio)propionate 7 With Somentioning

confidence: 99%

“…A colorless oil was recovered (0.12 g, 80%). 1 A solution of 1a (0.21 g, 0.9 mmol) in methanol (6 mL) was treated at room temperature with sodium methoxide (0.05 g, 0.9 mmol). GC monitoring of the reaction indicated that it was complete after 5-10 min.…”

Section: Oxidation Of Ethyl 3-(trifluoromethylthio)propionate 2a Intomentioning

confidence: 99%

“…Sodium or potassium trifluoromethanesulfinates (triflinates) are very valuable compounds which can be used either as precursors of trifluoromethanesulfonic acid, by oxidation with hydrogen peroxide [1], or as generators of trifluoromethyl radicals by single electron oxidation with tert-butyl hydroperoxide [2a]. In this latter way, sodium triflinate can be used to transform disulfides into trifluoromethyl sulfides [2] or to trifluoromethylate, in the presence of catalytic Cu(II) salts, electron-rich aromatics [3], enol acetates [4] or vinyl sulfides [5], in a ''pseudo-electophilic'' process.…”

Section: Introductionmentioning

confidence: 99%

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A new preparation of trifluoromethanesulfinate salts

Langlois¹,

Billard²,

Mulatier³

et al. 2007

Journal of Fluorine Chemistry

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“…The triflinate salt, which was transformed into triflic acid, was also obtained with sodium hydroxymethanesulfinate in anhydrous DMF (HOCH2S02-+ CF3Br ~ CF3S0n. 93 This reaction was applied to various RFI species 94 ; however, others reported that this condensation in aqueous DMF gives sodium perfluorocarboxylates (HOCH2S02-+ RpCF2I ~ RpC02 -)95. Transformation of the sulfinate to the carboxylate can result via photochemical electron transfer from the sulfinate to oxygen.…”

Section: Phosphorus Nucleophilesmentioning

confidence: 99%