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FUNCTIONALIZATION OF THE BICYCLO[3.2.1]-OCTADIENE SKELETON VIA PHOTOCATALYTIC OXYGENATION OF A (BENZO)FURAN DERIVATIVE


Vuk, Dragana; Kikaš, Ilijana; Ottó, Horváth; Škorić, Irena
FUNCTIONALIZATION OF THE BICYCLO[3.2.1]-OCTADIENE SKELETON VIA PHOTOCATALYTIC OXYGENATION OF A (BENZO)FURAN DERIVATIVE // XXIII. HRVATSKI SKUP KEMIČARA I KEMIJSKIH INŽENJERA, OSIJEK, 2013, Knjiga sažetaka / Hadžiev, Andrea ; Blažeković, Zdenko (ur.).
Zagreb: HDKI, Kemija u industriji, 2013. str. 160-160 (poster, domaća recenzija, sažetak, znanstveni)


Naslov
FUNCTIONALIZATION OF THE BICYCLO[3.2.1]-OCTADIENE SKELETON VIA PHOTOCATALYTIC OXYGENATION OF A (BENZO)FURAN DERIVATIVE

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

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
XXIII. HRVATSKI SKUP KEMIČARA I KEMIJSKIH INŽENJERA, OSIJEK, 2013, Knjiga sažetaka / Hadžiev, Andrea ; Blažeković, Zdenko - Zagreb : HDKI, Kemija u industriji, 2013, 160-160

ISBN
978-953-6894-50-5

Skup
XXIII. HRVATSKI SKUP KEMIČARA I KEMIJSKIH INŽENJERA

Mjesto i datum
Osijek, Hrvatska, 21.-24.04.2013

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
Photocatalytic oxygenation; Porphyrins; Benzobicyclo[3.2.1]octadienes; (Benzo)furan derivative

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 kationic and anionic free-base porphyrins 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 the 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 watersoluble 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. Annulation of a benzene to the outer side of the furan ring, however, led to the formation of only one type of product, independently of the photocatalyst used. Different oxygenation mechanisms leading to the same end-product, the 10-membered keto-lactone derivative, have been suggested for the metalloporphyrins and the corresponding free bases.

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

Profili:

Avatar Url Irena Škorić (autor)

Avatar Url Dragana Vuk (autor)

Citiraj ovu publikaciju

Vuk, Dragana; Kikaš, Ilijana; Ottó, Horváth; Škorić, Irena
FUNCTIONALIZATION OF THE BICYCLO[3.2.1]-OCTADIENE SKELETON VIA PHOTOCATALYTIC OXYGENATION OF A (BENZO)FURAN DERIVATIVE // XXIII. HRVATSKI SKUP KEMIČARA I KEMIJSKIH INŽENJERA, OSIJEK, 2013, Knjiga sažetaka / Hadžiev, Andrea ; Blažeković, Zdenko (ur.).
Zagreb: HDKI, Kemija u industriji, 2013. str. 160-160 (poster, domaća recenzija, sažetak, znanstveni)
Vuk, D., Kikaš, I., Ottó, H. & Škorić, I. (2013) FUNCTIONALIZATION OF THE BICYCLO[3.2.1]-OCTADIENE SKELETON VIA PHOTOCATALYTIC OXYGENATION OF A (BENZO)FURAN DERIVATIVE. U: Hadžiev, A. & Blažeković, Z. (ur.)XXIII. HRVATSKI SKUP KEMIČARA I KEMIJSKIH INŽENJERA, OSIJEK, 2013, Knjiga sažetaka.
@article{article, year = {2013}, pages = {160-160}, keywords = {Photocatalytic oxygenation, Porphyrins, Benzobicyclo[3.2.1]octadienes, (Benzo)furan derivative}, isbn = {978-953-6894-50-5}, title = {FUNCTIONALIZATION OF THE BICYCLO[3.2.1]-OCTADIENE SKELETON VIA PHOTOCATALYTIC OXYGENATION OF A (BENZO)FURAN DERIVATIVE}, keyword = {Photocatalytic oxygenation, Porphyrins, Benzobicyclo[3.2.1]octadienes, (Benzo)furan derivative}, publisher = {HDKI, Kemija u industriji}, publisherplace = {Osijek, Hrvatska} }