posted on 2016-02-18, 20:42authored byBelen Batanero, Fructuoso Barba, Avelino Martin
The one-pot concomitant electrochemical
reduction of phenanthrenequinones
(1, 2) and arenediazonium salts (3a–f) led to the formation of 1,3,4-oxadiazol-2(3H)-ones (4a–f, 5a) and dibenzo[c,e]azepines (6a–f) when N-methylformamide
was used as the solvent. A new pathway, different from those previously
described with other aprotic solvents, is proposed. The experimental
data support a radical mechanism for the electrochemical process followed
by an internal rearrangement to give the products.