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Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic and thermal oxygenation of a furan derivative


Kikaš, Ilijana; Horváth, Ottó; Škorić, Irena
Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic and thermal oxygenation of a furan derivative // Tetrahedron letters, 52 (2011), 47; 6255-6259 doi:10.1016/j.tetlet.2011.09.076 (međunarodna recenzija, članak, znanstveni)


Naslov
Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic and thermal oxygenation of a furan derivative

Autori
Kikaš, Ilijana ; Horváth, Ottó ; Škorić, Irena

Izvornik
Tetrahedron letters (0040-4039) 52 (2011), 47; 6255-6259

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

Ključne riječi
Benzobicyclo[3.2.1]octadienes; furan derivative; photocatalytic oxygenation; porphyrins

Sažetak
A simple and efficient protocol is utilized for the synthesis of novel functionalized benzobicyclo[3.2.1]octadiene derivatives by photocatalytic oxygenation of a furan derivative using an anionic free-base porphyrin as well as cationic and anionic manganese(III) porphyrins under different reaction conditions. The course and yields of these reactions were compared to those of the thermal reaction using m- chloroperbenzoic acid as oxidizing agent. The deviating reaction pathways with anionic and cationic metalloporphyrins may be attributed to simultaneous electronic and steric effects. Application of free-base and metalated water- soluble porphyrins for photocatalytic oxygenation of the furan ring fused to the rigid methano- bridged skeleton proved to be regioselective and flexible compared to the thermal reactions with mCPBA, giving at the same time novel potentially biologically active bicyclo[3.2.1]octenes with the basic skeleton of which is incorporated in many natural compounds.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
125-0982933-2926 - Heteropolicikli, strukturne osnove za bioaktivne spojeve. Sinteza i fotokemija (Irena Škorić, )

Ustanove
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Autor s matičnim brojem:
Irena Škorić, (235422)

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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