Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide (CROSBI ID 169973)
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Podaci o odgovornosti
Cindro, Nikola ; Horvat, Margareta ; Mlinarić-Majerski, Kata ; Griesbeck, Axel G. ; Basarić, Nikola
engleski
Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide
N-(4-homoadamantyl)phthalimide (5) on excitation and population of the triplet excited state underwent intramolecular H-abstractions and gave products 6 and 7. The major product, exo-alcohol 6 was a result of the regioselective δ H-abstraction and the stereoselective cyclization of the 1, 5-biradical. Minor products 7 were formed by photoinduced γ H-abstractions, followed by ring closure to azetidinols and ring enlargement to azepinediones. The observed selectivity to exo-alcohol 6 was explained by the conformation of 5 and the best orientation and the availability of the δ-H for the abstraction.
homoadamantanes ; photoinduced H-abstraction ; phthalimides
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