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

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

doi:10.3762/bjoc.7.36

Pregled bibliografske jedinice broj: 504685

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)

CROSBI ID: 504685 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

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

Projekti:
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Majerski, Kata, MZOS ) ( CroRIS)
02.05/25 - Fotokemija policikličkih molekula: od istraživanja mehanizama reakcije do novih lijekova i medicinskih primjena (Basarić, Nikola, HRZZ ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Margareta Sohora (autor)