“Elemental fluorine is one of the most chemically reactive substances known, due to the relative weakness of the F-F bond and the great strength of its bonds to most other elements, including hydrogen, carbon and silicon.”

 “Fluorine can behave both as a fluorinating agent and a powerful oxidant. It reacts readily with almost every other element and attacks many common materials, often with near- explosive violence.  In organic molecules, C-H bonds tend to be attacked indiscriminately by both free-radical and ionic mechanisms. Elemental fluorine has been successfully harnessed, notably by Chambers’ group,using strongly acidic, polar media to promote selective heterolyticfluorination and suppress the non-selective free-radical mode of reaction.  Other well-established techniques for moderating the reactivity of fluorineinvolve the use of inertdiluentsand very low temperatures. However, many alternative electrophilicfluorination reagents have been introduced with the objective of providing selectivity and ease of handling. N-Fluororeagents   A variety of N-fluorinated amines, quaternary salts, amides and sulfonamideshave been proposed as reagents for selective electrophilicfluorination under mild conditions (scheme 1). These are usually stable, easily-handled solids, and provide a range of fluorinating power from mild to moderate, depending on the structure of the reagent and the nature of the substrate. Another advantage is that, since free hydrogen fluoride is not a major by- product in fluorination reactions with this type of reagent, conventional glass equipment is often suitable.”

(Alfa Website, Fluorination, 11/17/2011)

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