Fluorinating agents perchloryl fluoride

There are two types of hypofluorite compounds that have been prepared, the perfluoroalkyl hypofluorites, such as CF3OF, and the acyl hypofluorites, such as CH3C02F. The fluorines of such compounds are very deshielded and thus have significantly positive chemical shifts (Scheme 7.15). Also shown is the powerful electrophilic fluorinating agent, perchloryl fluoride. 

The perchloryl fluoride [7616-94-6] FCIO, the acyl fluoride of perchloric acid, is a stable compound. Normally a gas having a melting poiat of —147.7° C and a boiling poiat of —46.7°C, it can be prepared by electrolysis of a saturated solution of sodium perchlorate ia anhydrous hydrofluoric acid. Some of its uses are as an effective fluorinating agent, as an oxidant ia rocket fuels, and as a gaseous dielectric for transformers (69). 

Electropositive fluorinating agents are categorized in distinct classes as (1) fluoroxy reagents, in which the fluorine is bound to an oxygen atom (for reviews, see references 1,2, 3, 4, 5, and 6) (2) fluoraza reagents, in which the fluorine atom is bound to the nitrogen atom of either an amide or ammonium ion structure (for a partial review, see reference 6), (3) xenon difluoride, in which the fluorine atoms are bound to xenon (for reviews, see references 5, 7, 8, and 114) and (4) perchloryl fluoride, in which the fluorine atom is bound to the chlorine atom of the perchloryl function (for a review, see reference 9). 

These electrophilic fluorinating agents arc not easy to handle thus, e.xploxions may occur when liquid perchloryl fluoride comes in contact with organic material. or when difluorodiazene changes state (i.e., gas to liquid or solid in a reflux condenser)."" Full safety precautions, such as the use of safety screens, are recommended moreover, due to the toxicity of these agents, reactions should be carried out under efficient hoods. 

Other powerful fluorinating agents, such as trifluoromethyl hypofluorite, perchloryl fluoride and acetyl hypofluorite (CF3OF, FCIO3, AcOF) have been used successfully, but are not easy to obtain, are toxic and the last two are intrinsically explosive. Some newer, milder, but more limited, fluorinating agents are discussed later in this section. 

A variety of compounds has been used as halogenation agents [3]. Fluorination can be performed with molecular fluorine (F2), HF, fluoroxy compounds, XeFi, perchloryl fluoride (FCIO3) and metallic fluorides (especially CrF3 and AIF3 or their mixtures). Apart from molecular chlorine and HCl, other popular chlorina-... 

Alkali attacks FCIO3 only slowly, even at 500 K. Perchloryl fluoride is a mild fluorinating agent and has been used in the preparation of fluorinated steroids. It is... 

MONOPHENYLHYDRAZINE (100-63-0) A highly reactive reducing agent. Combustible solid (flash point 190°F/88°C). Dust or powder forms explosive mixture with air. Reacts violently with oxidizers calcium hypochlorite, fluorine, hydrogen peroxide, perchlorates methyl iodide, 2-phenylamino-3-phenyloxazirane, 3-(3-cyano-l,2,4-oxadiazol-5-yl)-4-cyanofurazan-2-(5-) oxide, dicyanofurazan, dicyanofurazan-n-oxide, lead dioxide. Mixture with perchloryl fluoride forms an explosive material. Incompatible with oxides of iron. 

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