Antimony fluorides, reaction with organic

Organic fluorine compounds were first prepared in the latter part of the nineteenth century. Pioneer work by the Belgian chemist, F. Swarts, led to observations that antimony(Ill) fluoride reacts with organic compounds having activated carbon—chlorine bonds to form the corresponding carbon—fluorine bonds. Preparation of fluorinated compounds was faciUtated by fluorinations with antimony(Ill) fluoride containing antimony(V) haUdes as a reaction catalyst. 

Hydrogen fluoride alone undergoes exchange reactions only with very reactive organic halides. However,. because it reacts with antimony chloride to form antimony fluoride and hydrogen chloride,34 it can be used to transform a large amount of organic halide to the fluoride with the aid of only small.amounts of antimony salts. This is the method used in industry for the preparation of dichlorodifluoromethane.34-36... 

Tetrakis(phenyldifluorophosphine)nickel-(0) could also be obtained, using arsenic trifluoride in the presence of catalytic amounts of antimony pentachloride, or zinc fluoride as fluorinating agents. Yields as high as 50% could be obtained, but sizable decomposition on the process of fluorination of the chlorophosphine nickel-(0) complexes in solution could not be entirely suppressed. The marked instability of zerovalent nickel-phosphine complexes in solution in organic solvents, even under strictly anhydrous and anaerobic conditions, has been noted by several workers (16,20), but is still lacking a detailed explanation. A closer examination of the system carbon tetrachloride-tetrakis(trichlorophosphine)nickel-(0) (23) showed the main pa h of the reaction to consist in the formation of hexachloro-ethane with conversion of zerovalent into bivalent nickel, while the coordinated... 

Covalent fluorides of group 3 and group 5 elements (boron, tin, phosphorus, antimony, etc) are widely used in organic synthesis as strong Lewis acids Boron trifluoride etherate is one of the most common reagents used to catalyze many organic reactions. A representative example is its recent application as a catalyst in the cycloadditions of 2-aza-l,3-dienes with different dienophiles [14] Boron trifluoride etherate and other fluormated Lewis acids are effective activators of the... 

Organic compounds Organic fluorine compounds arc made by reaction of the corresponding alkane chloro-compounds with silver fluoride, mercurous fluoride, antimony trifluoride, titanium tetrafluoridc. and the arene fluoro-compounds by the diazo-reaction using hydrogen fluoride, and otherwise. The effect of the continued replacemenl of hydrogen atoms by fluorine atoms is an initial increase in reactivity, followed by a reversal of this effect, so lhal the highly substituted compounds arc relatively inert, See also Fluorocarbon. 

SWARTS REACTION. Fluorination of organic polyhalides with antimony trifluoride (or zinc and mercury fluorides) in the presence of a trace of a pentavalent antimony salt. 

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