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How Trimethyl(trifluoromethyl)silane Reacts With Itself in the Presence of Naked Fluoride--A One-Pot Synthesis of bis([15]crown-5)cesium 1,1,1,3,5,5,5-heptafluoro-2,4-bis(trifluoromethyl)pentenide

How Trimethyl(trifluoromethyl)silane Reacts With Itself in the Presence of Naked Fluoride--A One-Pot Synthesis of bis([15]crown-5)cesium 1,1,1,3,5,5,5-heptafluoro-2,4-bis(trifluoromethyl)pentenide

Wieland Tyrra, Mikhail M Kremlev, Dieter Naumann, Harald Scherer, Harald Schmidt, Berthold Hoge, Ingo Pantenburg, Yurii L Yagupolskii

Chemistry. 2005 Nov 4;11(22):6514-8.

PMID: 16121407

Abstract:

Reactions of trimethyl(trifluoromethyl)silane in the presence of "naked" fluoride proceed up to a temperature of +5 degrees C mainly with formation of [Me3Si(CF3)2]-. A further rise of temperature up to about 20 degrees C gives evidence for the formation of a salt with the 1,1,1,2,3,6,6,6-octafluoro-2,4,4,5,5-pentakis(trifluoromethyl)hexan-3-ide anion. This intermediate decomposes at room temperature into the 1,1,1,3,5,5,5-heptafluoro-2,4-bis(trifluoromethyl)pentenide anion. The bis([15]crown-5)cesium salt, [Cs([15]crown-5)2][(CF3)2CCFC(CF3)2] has been characterized unambiguously as the stable final product of this reaction sequence. Thermal decomposition of this salt opens a convenient nontoxic route to obtain 1,1,3,3-tetrakis(trifluoromethyl)allene, (F3C)2C=C=C(CF3)2.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP81290202	Trimethyl(trifluoromethyl)silane		81290-20-2	Price

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