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


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 (međunarodna recenzija, članak, znanstveni)


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

Autori
Cindro, Nikola ; Horvat, Margareta ; Mlinarić-Majerski, Kata ; Griesbeck, Axel G. ; Basarić, Nikola

Izvornik
Beilstein journal of organic chemistry (1860-5397) 7 (2011); 270-277

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Homoadamantanes ; photoinduced H-abstraction ; phthalimides

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
02.05/25
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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