Fluorination of organic compounds

Fluorination of organic compounds using high valency metallic fluorides (14) may be represented as follows ... 

Table 1. Direct Fluorination of Organic Compounds Using Batch Reaction Techniques...

The Exhaustive Fluorination of Organic Compounds by High Valency Metal Fluorides, M. Stacey and J. C. Tatlow, Adv. Fluorine Chem., 1 (1960) 166-198. 

Antimony pentafluoride is used as a fluorinating agent for fluorination of organic compounds. 

S. Rozen, Elemental fluorine as a legitimate reagent for selective fluorination of organic compounds, Acc. Chem. Res. 21 (1988) 307-312. 

G.S. Lai, Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1, 4-diazabicyclo[2.2.2]octane salts (selectfluor reagents), J. Org. Chem. 58 (1993) 2791-2796. 

Meinert and others [85] have stated that their concept for the electrochemical fluorination of organic compounds is based on the assumption that the first step is the anodic oxidation of the organic molecule. The electrochemical process is promoted by weakening of the C-H bonds due to hydrogen-fluorine bridges. After anodic withdrawal, the C-F bond is formed by insertion of a fluoride ion, present in the Helmholtz-double-layer at the electrode surface. 

Hydrocarbons inflame spontaneously in F2, giving fluorocarbons and HF. Controlled fluorination of organic compounds is possible by electrolyzing them in liquid HF (bp 20 °C) at a nickel anode, at voltages just below that needed to evolve F2 ... 

The anodic partial fluorination of organic compounds occurs in weak Lewis base solvents (AN, CH2CI2, DME) containing fluoride ions (QH Ia QH + e f H+ Q - F or QH -e-H+ > Q+ — - Q - F. This occurs because F in aprotic solvents is ex... 

Direct fluorination of organic compounds using fluorine is an important methodology when considering safety, environmental and recycling problems. Fluorine can be fed into the reactor from a cylinder for the direct fluorination procedure, but this method has economic and safety disadvantages. Electrochemical generation of fluorine has recently been adopted for fluorination even in the laboratory. It can be operated easily and safely, because operational difficulties have been improved. 

Table 6. Fluorination of Organic Compounds with 1-Fluoropyridinium Pyridine Heptafluorodiborate (NFPy, 33) in Acetonitrile69...

Mercury(II) fluoride is a white, fluffy powder, extremely sensitive to moisture. In the presence of water, a dihydrate salt forms. If the salt is to be used for the fluorination of organic compounds, it must be kept rigorously dry.55 Earlier work is described in Houben-Weyl, Vol. 5/3, p 197. 

Elemental Fluorine as a Legitimate Reagent for Selective Fluorination of Organic Compounds ... 

Novel Methods for Selective Fluorination of Organic Compounds. Design and Synthesis of Fluonnated Antimetabolites Kollonitsch, J hr J Chem 17, 53-59 50... 

G. G. Furin, "Synthetic Aspects of the Fluorination of Organic Compounds, Vol 16, Part 1, Soviet Scientific Reviews, Section B, Harwood Academic Publishers, Reading, Berkshire, U. K. (1991)... 

The generation of (difluoroiodo)arenes by anodic oxidations of aryl iodides in the presence of excess Et3N nHF is a notable recent development (Scheme 31) [96,97]. Because the fluoroiodanes are activated by hydrogen-bonding with HF, such reagent combinations are especially useful for electrophilic fluorinations of organic compounds. When oxidation potentials of the aryl iodides are lower than those of the substrates, indirect anodic fluorinations of the latter can be achieved. 

As with the other first-row elements, much of the chemistry of fluorine stands distinctly apart from that of its congeners. Anomalous effects are due partially to the extreme electronegativity of fluorine, partially to the inability for the fluorine octet to expand, and partially to the small size of the atom. The low F—F bond energy, coupled with the high energy of bonds formed between fluorine and other elements, makes many of the reactions of the F2 greatly exothermic, and a number take place with almost explosive violence. (Fluorination of organic compounds with undiluted fluorine, for instance, can be particularly hazardous.)... 

Fluorination of organic compounds with nickel fluorides... 

Fullerene Cgo is easily fluorinated by elemental fluorine at temperatures less than 100°C [29,30] probably because of its nearly spherical surface and exposed it bonding. Direct fluorination of organic compounds by fluorine gas demonstrated that fluorine was preferentially bonded to a carbon atom with a high electron density [31,32], This may be a main reason why fullerene C60 is more easily fluorinated than graphite. On the contrary, the fluorination behavior of carbon nanotube is similar to that of graphite as already shown. 

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