Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide

• Nikola Cindro,
• Margareta Horvat,
• Kata Mlinarić-Majerski,
• Axel G. Griesbeck and
• Nikola Basarić

Beilstein J. Org. Chem. 2011, 7, 270–277, doi:10.3762/bjoc.7.36

• for the abstraction. Keywords: homoadamantanes; photoinduced H-abstraction; phthalimides; Introduction Since the pioneering work of Ciamican and Paterno [1][2], the photochemistry of ketones has been intensively studied [3][4][5][6]. One important chemical pathway for the deactivation of ketones

• products [34]. Furthermore, suitably substituted phthalimides deactivate from the excited state by intramolecular H-abstractions to yield cyclization products, often benzazepinone derivatives [35][36][37]. Therefore, photoinduced homolytic C–H activation by phthalimide derivatives can, in principle, be

• protic solvent, undergoes H-abstraction to give products with ten times higher quantum yields than in an aprotic solvent. Such a finding is in accordance with previous reports for phthalimides and is probably due to a switching of the relative order of the singlet and the triplet excited states of the