Photoreactions of cyclic imides. Examples of synthetic organic photochemistry

Abstract

Photochemistry in recent years has extended the armamentarium of the organic chemist in coping with synthetic challenges.1 Novel chromophoric systems have been developed and designed, and reactivities of excited states have been defined and utilized. The technique of selective quenching has made possible bond formation and fragmentation leading to molecular structures which would be not readily accessible by recourse to conventional reactions proceeding through ground-state paths.1,2 Probably the most active area of organic photochemistry has been the study of systems which possess a carbonyl group.3 As a result, a

Radical ion cyclizations

“…The photochemistry of imides, especially of the N-substituted phthalimides, has been studied intensively by several research groups during the last two decades [233][234][235]. It has been shown that the determining step in inter-and intramolecular photoreactions of phthalimides with various electron donors is the electron transfer process.…”

Addition and cycloaddition reactions via photoinduced electron transfer

“…However, the photoreaction in organic solvents proceeds via the exciplex to give the different cyclized products. Kanaoka electron transfer reaction of S-methyl compounds [70]. In this case, deprotonation from the a-carbon of the S-methyl group in the radical cation occurs to give the S-CH~ radical which cyclizes to give the cyclic thio compounds.…”

A strategy for the preparation of cyclic polyarenes based on single electron transfer-promoted photocyclization reactions

“…? 1.6 V) [21][22][23] that have appropriate reduction potentials. In addition, desilylation of benzyl silane radical cations should take place rapidly to form benzyl radicals that can undergo C-C bond forming reactions.…”