Naslov
Photodecarboxylation of adamantane amino acids activated by phthalimide

Autori
Mandić, Leo ; Mlinarić-Majerski, Kata ; Griesbeck, Axel G ; Basarić, Nikola

Izvornik
European journal of organic chemistry (1434-193X) 2016 (2016); 4404-4414

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

Ključne riječi
Adamantane amino acids ; Photodecarboxylation ; Phtalimide ; Photochemical reaction

Sažetak
Adamantane α-, β- and δ-amino acids activated by phthalimide 3-6 were synthesized and their photochemical reactivity in photodecarboxylation reactions was investigated. All amino acid derivatives 3-6 undergo photoinduced electron transfer (PET) and decarboxylation, most probably via the triplet excited states. For β-amino acid derivatives, the decarboxylation is accompanied by a cyclization giving complex polycyclic molecules with potential biological interest. The adamantyl radical formed by photoinduced decarboxylation can be trapped by alkenes or oxygen delivering adducts or alcohols, respectively. The photodecarboxylation is generally more efficient under acetone sensitization conditions (with quantum yields, Φ = 0.02-0.5), then upon direct excitation, and depends on the chain length (intramolecular distance) between the electron donor (carboxylate) and the acceptor (phthalimide in the triplet excited state). Formation of different radicals, 1-adamantyl or 2-adamantyl, most probably does not affect the overall decarboxylation reaction rate. The reactivity is mostly governed by the distance between the electron donor and the acceptor. The current report is important for the better understanding of the photodecarboxylation, and rational design of molecular systems undergoing photoinduced decarboxylation and cyclization.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA