Arylsilver compounds

Diarylzinc compounds react with silver salts to give arylsilver compounds of high purity and stability (Scheme 1.15).52 Van der Kerk and coworkers synthesized phenylsilver and a number of methyl-substituted arylsilver compounds via this route, and found that ortho-methy substitution significantly increased the thermal stability of the compound, as is the case for the corresponding arylcopper compounds (Table 1.5).53... 

The arylsilver compounds formed by interaction of an aryl Grignard reagent with a silver(I) halide can be isolated as solids which are stable for a short time at room temperature. Thus, for example, PhAg was first obtained as a dark solid which upon drying out decomposed, sometimes with explosive violence, to give silver metal and biphenyl12. The... 

Arylsilver compounds are likewise air, moisture and light sensitive, but are sufficiently thermally stable and thus could be isolated and characterized in selected cases. The first synthesis of an arylsilver species was reported in 1919 by Krause and Schmitz, who studied the reaction of silver nitrate with alkyl aryllead or -tin compounds in alcohol solution and obtained bright yellow precipitates of the composition (PhAg)2 AgN03 (equation 22)59. 

Arylsilver compounds ArAg, where the aryl group carries one or two substituents containing a heteroatom, have been obtained by transmetallation reactions of silver bromide with the corresponding organolithium compounds 2-[(dimethylamino)methyl]phenyl silver (17)70, (2,6-dimethoxyphenyl)silver (18)70 71 and (2,4,6-trimethoxyphenyl)silver (19)70. The compounds show an enhanced thermal stability with decomposition temperatures well above 150 °C. 

In contrast to the air and moisture sensitivity of most simple arylsilver compounds, perhalogenated aromatic silver compounds are usually stable to water and oxygen. 

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