Photooxygenation of indolizines (heterocyclic aromatic derivates of indole) has been investigated in both mechanistic and synthetic contexts. Rather than proceeding through a Type I or Type II photooxygenation mechanism, some investigators have chosen to use 9,10-dicyanoanthracene (DCA) as a photosensitizer, leading to the reaction of an indolizine derivative with the superoxide anion radical. Note that the reaction proceeds through an indolizine radical cation intermediate that has not been isolated (and thus is not depicted):