Fluonnating agent

Fluorinatton of graphite with fluorine gives graphite fluorides that have interesting properties, as recently reviewed [63]. Pyridine and its derivatives add elemental fluorine to form unstable N-fluoro adducts [14, 26, 64, 65]. These may decompose to 2-fluoropyndines [65] or be stabilized by treatment with inflate salts to form useful electrophilic fluonnating agents [64]... 

On the other hand, oxidizing fluonnating agents like silver difluoride, xenon difluoride, or bromine trifluoride replace one chlorine group and then cleave the sulfur-nitrogen bond [56],... 

The mixture was kept at 40-50 C for 3 h and then overnight at room temperature Dibenzyl ether (25%) was isolated Nitrobenzyl fluorides are obtained by adding the alcohol to an excess of the fluonnating agent When hexafluoropropyldiethylamine is added to the alcohol, dibenzyl ethers are formed exclusively ... 

Reactions of polyhydroxyl compounds such as carbohydrates with DAST lead to replacement of one or two hydroxyl groups by fluorine, more fluorine atoms are not introduced even when a large excess of the reagent is used [132, 139, 147] Although diethylaminosulfur tnfluonde (DAST) is the most popular, other dialkylaminosulfuranes, such as diisopropylamino- [95] pyrrolidino [95 109 /27], dimethylamino- [148], piperidino- [148] and particularly morpholinosulfur trifluonde [148,149, ISO], are also used as fluonnating agents to convert alcohols into fluorides... 

Depending on the fluonnating agent, diazoalkanes, diazoketones, and diazoesters can undergo hydrofluorination, halofluonnation, and geminal difluonnation reactions... 

Mukhametshin, F M New Fluonnating Agents in Organic Synthesis Springer-Verlag Berlin 1989, p 69... 

Mixtures of anhydrous hydrogen fluoride and tetrahydrofuran are successfully used as fluonnating agents to convert 1,1,2-trifluoro-l-alken-3-ols, easily prepared from bromotrifluoroethene via lithiation followed by the reaction with aldehydes or ketones, to 1,1, l,2-tetrafluoro-2-alkenes The yields are optimal with a 5 1 ratio of hydrogen fluoride to tetrahydrofuran The fluonnation reaction involves a fluoride ion-induced rearrangement (SN2 mechanism) of allylic alcohols [65] (equation 40)... 

Phosphorus-nitrogen compounds containing alkylated amino groups can be cleaved by fluonnating agents Phenyldifluorophosphine is formed from the reaction of fV.MA. A -tetramethylphenylphosphonous amide and benzoyl fluoride [79] (equation 17). 

Fluonnated agents such as flurbiprofen (11), flunisal(I2), diflunisal (13), and sulindac (14), acting as prostaglandin synthesis inhibitors, have been available for some time [5] The recent introduction of flunoxaprofen (IS), a lipoxygenase inhibitor, is notable It reportedly produces considerably less severe gastric disturbance [23]... 

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