Organic perchloryl compounds

This is a new class of compounds recently obtained and described by Inman, Oesterling and Tyczkowski [46]. They are characterized by the presence of the perchloryl group (C103) and their general formula is RC103. So far only aromatic derivatives of this kind are known. 

They are formed by a Friedel-Crafts type of reaction between perchloryl fluoride (CIO3F) and aromatic compounds  

A number of perchloryl compounds were prepared by this method with a good yield. 

No data on their explosive properties are available, but they are reported to be sensitive to shock and high temperature. 

It can be hydrolysed with potassium hydroxide solution to yield potassium chlorate and phenol. When reduced with hydrogen on palladium it yielded benzene, HC1 and water [53]. 

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Procedures relevant to safe handling and use are discussed. Perchloryl fluoride is stable to heat, shock and moisture, but is a powerful oxidiser comparable with liquid oxygen. It fonns flammable and/or explosive mixtures with combustible gases and vapours [1,2]. It only reacts with strongly nucleophilic centres, and the by-product, chloric acid is dangerously explosive in admixture with organic compounds [3], Safety aspects of practical use of perchloryl fluoride have been reviewed [4],... 

Still another compound of great interest is perchloryl fluoride (C103 F). It was described in Vol. II. Perchloryl fluoride is distinguished by its high stability it causes no corrosion of commonly used materials. It reacts vigorously with oxidizable organic compounds. 

Perchloryl fluoride is thermally stable up to 500° C. and very resistant to hydrolysis. It is a colorless gas in ordinary conditions with b.p., —46.7°C., and m.p., —147.8°C. It is a powerful oxidant at elevated temperatures. It exhibits selective fluorination properties and has been used as a perchlorylation reagent for introducing the C103 group on carbon in organic compounds. It is moderately toxic (maximum allowable concentration, 3 p.p.m.8). A comprehensive review of the production, physical properties, and reactions of perchloryl fluoride is available.9... 

Fluorinations using perchloryl fluoride (FCIO3) have been reported [17, 142] but, since the perchloric acid that is formed as a side-product gives an explosive mixture with organic compounds, this approach to selective fluorinations is not recommended. 

ANILINE (62-53-3) Combustible liquid (flash point 158°F/70°C). Unless inhibited (usually by methanol), readily able to polymerize. Violent reaction, including the possibility of fire, explosion, and the formation of heat- or shock-sensitive compounds may result from contact with acetic anhydride, benzene diazonium-2-carboxylate, aldehydes, alkalis, benzenamine hydrochloride, boron trichloride, l-bromo-2,5-pyrrolidinedione, chlorosulfonic acid, dibenzoyl peroxide, fluorine nitrate, halogens, hydrogen peroxide, isocyanates, oleum, oxidizers, organic anhydrides, ozone, perchloryl fluoride, perchromates, potassium peroxide, P-propiolactone, sodium peroxide, strong acids, trichloromelamine. Strong reaction with toluene diisocyanate. Reacts with alkaline earth and alkali metals. Attacks some plastics, rubber, and coatings. Incompatible with copper and copper alloys. 

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