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Synthesis and photochemistry of activated adamantyl amino acids


Mandić, Leo; Mlinarić-Majerski, Kata; Basarić, Nikola
Synthesis and photochemistry of activated adamantyl amino acids // Simpozij studenata doktorskih studija PMF-a
Zahreb, Hrvatska: Prirodoslovno-matematički fakultet Sveučilišta u Zagrebu, 2016. (predavanje, domaća recenzija, sažetak, ostalo)


Naslov
Synthesis and photochemistry of activated adamantyl amino acids

Autori
Mandić, Leo ; Mlinarić-Majerski, Kata ; Basarić, Nikola

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

Izvornik
Simpozij studenata doktorskih studija PMF-a / - : Prirodoslovno-matematički fakultet Sveučilišta u Zagrebu, 2016

ISBN
978-953-6076-39-0

Skup
Simpozij studenata doktorskih studija PMF-a

Mjesto i datum
Zahreb, Hrvatska, 26.02.2016

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Domaća recenzija

Ključne riječi
Photodecarboxylation ; photoinduced electron transfer (PET) ; phtalimide

Sažetak
Phthalimide is a useful chromophore which undergoes different photochemical reactions, including photoinduced electron transfer (PET) [1]. In PET reactions, phthalimide in the triplet excited state acts as an electron acceptor, whereas, for example, carboxylate group can be electron donor [2]. Such a PET reaction initiates photodecarboxylation that ultimately gives cyclization or radical trapping products [3]. Photodecarboxylation has been intensively studied because of the potential application in organic synthesis [4], as well as due to severe side effects of some nonsteroidal non-inflammatory drugs which cause photoalergies upon photodecarboxylation [5]. Herein we report synthesis and investigation of photochemical reactivity of activated adamantyl amino acids 1-5. All investigated molecules undergo PET and decarboxylation. The study is conducted to get an understanding on the effects of the adamantyl rigid spacer between the donor and the acceptor on the efficiency of PET and decarboxylation. Moreover, in some examples photodecarboxylation leads to the formation of very complex polycyclic structures whose synthesis would be very demanding without the photochemical key step.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (Nikola Basarić, )

Ustanove
Prirodoslovno-matematički fakultet, Matematički odjel, Zagreb,
Institut "Ruđer Bošković", Zagreb