ABSTRACT
In terms of synthetic applications, the phthalimide system has attracted much attention over the past three decades, as noticeable by a number of summarizing reviews.
Although the photochemistry of phthalimide derivatives is similar to that of carbonyl compounds, it covers additional reactivity features due to the remarkably high oxidizing power of the excited singlet and triplet states. Thus, the presence of energetically feasible electron donor groups leads to the generation of radical ions that can undergo nonproductive (back) electron transfer, direct radical ion combination, or mesolytic extrusion of a suitable leaving group (e.g., a proton, silyl cation, or carbon dioxide), respectively. The competition between these processes can be controlled by varying the redox potentials, the stability of the radical cations, and the leaving group ability.
