Abstract
The mechanism of the anodic cyanation of aromatic compounds has been investigated, using the determination of isomer distributions as an experimental tool. The reaction has the general characteristics of a homogeneous electrophilic substitution process, being highly selective with regard to attack at the ring positions in monosubstituted aromatic substrates. Nuclear substitution is highly favoured over side-chain substitution in alkylaromatic compounds, such as toluene and mesitylene. For comparison, a study of a homolytic cyanation reaction has been performed. The data obtained, as well as the comparison with the anodic acetoxylation reaction, are in agreement with a mechanism involving a cyanide ion assisted two-electron transfer from the aromatic compound to the anode as the product-forming step.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
