Notification about the Explosive Properties of Togni’s Reagent II and One of Its Precursors

Fiederling, Nikolaus; Haller, Jan; Schramm, Heiko

doi:10.1021/op400035b

Cited by 56 publications

(40 citation statements)

References 3 publications

(5 reference statements)

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“…Diiodoacetylene ( 17 )35a and bis(pentafluorophenyl)acetylene ( 14 )35b were synthesized by literature procedures. Compounds 14 , 17 and Togni’s Reagent should be handled with special care due to their toxicity and explosive nature 29b. Xenon difluoride was obtained from the elements49 or purchased from Sigma‐Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Fluorinated and Trifluoromethylated Corannulenes

Schmidt

Topolinski

Yamada

et al. 2013

Chemistry A European J

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The syntheses and properties of corannulenes carrying electron-withdrawing groups (F, CF3 , C6 F5 ) are reported. Direct fluorination of corannulene (C20 H10 ) was carried out with xenon difluoride, and the crystal structure of the product was confirmed by the X-ray analysis. Novel trifluoromethylated corannulenes, including the versatile 4,9-dibromo-1,2-bis(trifluoromethyl)corannulene, were obtained by various established ring-closing reactions. Besides the use of hexafluorobutyne for the construction of fluoranthenes by Diels-Alder reaction as precursor molecules to form 1,2-disubstituted corannulenes, bis(pentafluorophenyl)acetylene was employed as dienophile. The molecular structure and crystal packing of a trifluoromethylated corannulene was determined by single-crystal X-ray analysis and compared with those known brominated and trifluoromethylated corannulenes. The general electron-acceptor properties of corannulenes bearing substituents introduced in particular positions by liquid-phase synthesis are discussed together with published computational results.

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Section: Methodsmentioning

confidence: 99%

Fluorinated and Trifluoromethylated Corannulenes

Schmidt

Topolinski

Yamada

et al. 2013

Chemistry A European J

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“…[15] However, its synthesis appears to be not so easy to perform and its stability seems limited. Furthermore, the recent emphasis on the explosive character of trifluoromethylated hypervalent iodine reagents [16] suggests that such a derivative may pose a similar danger. Finally, stable trifluoromethanesulfenamides have also demonstrated their potential in electrophilic trifluoromethylthiolation reactions of various classes of compounds.…”

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confidence: 99%

Base‐Catalyzed Electrophilic Trifluoromethylthiolation of Terminal Alkynes

2013

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“…Togni's reagents were reported to be explosive, and should only be handled with the appropriate knowledge and safety measures. 31 Togni's reagent 1, which showed a decomposition energy of 502 J/g in the DSC-measurement, is dangerously explosive and may only be transported by approval of the national competent authority. Another critical property of Togni's reagent 1 is the fast combustion when ignited.…”

Section: Methodsmentioning

confidence: 99%

“…The substance vaporizes quickly without flame when ignited with a match corresponding to a combustion factor BZ6 which is the same classification as that of black powder. 31 Togni's reagent 2 produces a melting signal with an onset at 77 °C followed by a decomposition with a strong exotherm of 790 J/g with an onset at 135 °C and a maximum heat flow of 6 W/g in an aluminum pan with pierced lid. …”

Section: Methodsmentioning

confidence: 99%