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Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide (CROSBI ID 169973)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Cindro, Nikola ; Horvat, Margareta ; Mlinarić-Majerski, Kata ; Griesbeck, Axel G. ; Basarić, Nikola Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide // Beilstein journal of organic chemistry, 7 (2011), 270-277. doi: 10.3762/bjoc.7.36

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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Podaci o izdanju

7

2011.

270-277

objavljeno

1860-5397

10.3762/bjoc.7.36

Povezanost rada

Kemija

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