1‐Bromo‐3,5‐bis(trifluoromethyl)benzene: A Versatile Starting Material for Organometallic Synthesis

Porwisiak, Jacek; Schlosser, Manfred

doi:10.1002/cber.19961290219

Cited by 25 publications

(12 citation statements)

References 15 publications

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“…[70] Pure 3,5-bis(trifluoromethyl)phenyllithium can be generated by halogen/metal interconversion between 1-bromo-3,5-bis(trifluoromethyl)benzene and butyllithium (LIC) in diethyl ether. [108] …”

Section: Meta-substituted (Trifluoromethyl)benzenesmentioning

confidence: 97%

Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH, NH, and CH Acidities

Schlosser¹

1998

Angewandte Chemie International Edition

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284

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Fluorine, the heterosubstituent par excellence, which can have a stronger impact on the reactivity in its vicinity than any other element, may serve as a crucial test of any model of the origin and transmission of electronic effects. To what extent fluoro substituents in organic compounds (A-H) increase their kinetic proton mobility (H/D and H/metal (M) exchange) and thermodynamic acidity in aqueous media and in the gas phase (see below) depends on many factors such as induction, resonance, polarization, hyperconjugation, and dipolar interactions.

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Section: Meta-substituted (Trifluoromethyl)benzenesmentioning

confidence: 97%

Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH, NH, and CH Acidities

Schlosser¹

1998

Angewandte Chemie International Edition

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284

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“…According to the literature, the allylation of halogenobenzenes has been achieved, usually with modest yields, via the formation of organoderivatives of a variety of metals, such as Mg,20–23 Li,22, 24–26 and Yb 27. In a first attempt, we prepared the Grignard derivative of compound III by a reaction with magnesium in refluxing anhydrous THF (Scheme and Table 1, entry 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1,3‐bis(2‐trimethylsilyloxyhexafluoro‐2‐propyl)‐5‐allylbenzene and its introduction into polysiloxane chains

Boutevin

Gaboyard

Guida‐Pietrasanta

et al. 2003

J. Polym. Sci. A Polym. Chem.

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The synthesis of 1,3-bis(2-trimethylsilyloxyhexafluoro-2-propyl)-5-allylbenzene (IV) is described, starting from commercially available 1,3-bis(2-hydroxyhexafluoro-2-propyl)benzene. After the first step of iodination was optimized, a series of metallating agents were tested, before allylation, so that the best reagent could be selected. The allyl compound IV was then added to two different copoly(dimethylmethylhydro)siloxanes, PS 122.5 and PS 123 from Gelest/ABCR, via platinum-catalyzed hydrosilylation, for the preparation of new polysiloxanes bearing specifically designed pendant aryl moieties. The different synthesized products were characterized by spectroscopic methods (IR and 1 H, 13 C, 19 F, and 29 Si NMR), and the glass-transition temperatures of copolymers VI-2, VI-3, and VI-4 were measured. It was shown that the higher the amount was of grafted fluoroaryl groups, the higher the glass-transition temperature was.

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“…[70] Reines 3,5-Bis(trifluormethyl)phenyllithium kann durch Halogen/Metall-Austausch zwischen 1-Brom-3,5-bis(trifluormethyl)benzol und Butyllithium (LIC) in Diethylether erzeugt werden. [108] 6. Schluûfolgerungen und Ausblick Acidität ist nicht nur eine physikochemische Schlüsseleigenschaft, sondern steuert oft auch die Reaktivität und Bioaktivität.…”

Section: M-substituierte Trifluormethylbenzoleunclassified

Parametrisierung von Substituenten – der Einfluß von Fluor und anderen Heteroatomen auf OH-, NH- und CH-Aciditäten

Schlosser

1998

Angewandte Chemie

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Stärker als jedes andere Element vermag Fluor als Substituent die Reaktivität in seiner Umgebung zu verändern und dient daher als Prüfstein für Modelle, die Ursache und Übertragung elektronischer Effekte zu beschreiben versuchen. Wie stark Fluorsubstituenten in organischen Verbindungen (A−H) deren kinetische Protonenbeweglichkeit (H/D‐ und H/Metall(M)‐Austausch) und thermodynamische Acidität in wäßrigen Medien und in der Gasphase (siehe unten) erhöhen, hängt von vielen Faktoren wie induktiven, mesomeren, polarisierenden, hyperkonjugativen und dipolaren Wechselwirkungen ab.

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1‐Bromo‐3,5‐bis(trifluoromethyl)benzene: A Versatile Starting Material for Organometallic Synthesis

Abstract: Optional site selectivity can be established in numerous neighboring group-assisted metalation reactions of arenes by mechanism-based substrateheagent matching" p31.

Cited by 25 publications

References 15 publications

Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH, NH, and CH Acidities

Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH, NH, and CH Acidities

Synthesis of 1,3‐bis(2‐trimethylsilyloxyhexafluoro‐2‐propyl)‐5‐allylbenzene and its introduction into polysiloxane chains

Parametrisierung von Substituenten – der Einfluß von Fluor und anderen Heteroatomen auf OH-, NH- und CH-Aciditäten

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