[bpyfiend]

I've been working on learning nitrile and isonitrile synthesis.  I read recently that isocyanides were first synthesized with silver cyanide and an alkyl halide.

It seems that the silver ion has enough steric bulk that it prevents the formation of the nitrile (as the smaller KCN and NaCN ions do).

I'm wondering then if a similar reaction would work on an aryl halide.  It seems that it would work like a normal SnAR reaction.  I mean, you can make Grignards, or turn the halide to a phenol with sodium bicarbonate. 

It seems like you should be able to refulx trichlorobenzene with an excess of silver cyanide, and silver chloride would precipitate. 

feasible? stupid? 

[orgopete]

Nucleophilic substitution reactions on aromatic rings usually go via benzyne or addition-elimination. Therefore, trichlorobenzene does not seem likely to react via either of those two mechanisms.

[zengjia1029]

I think the metal ion maybe play an important role in this transfermation. also I guess the machanism here is very similar to the Rosenmund-Von Braun reaction.

[orgopete]

I suspected a mechanism such as that posted by zengjia might be possible, hence I tried to be careful in my comparisons.

Kudos to zengjia!