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Pregled bibliografske jedinice broj: 571702

Zbornik radova

Autori: Cindro, Nikola; Mlinarić-Majerski, Kata; Halasz, Ivan; Griesbeck; Axel G.; Basarić, Nikola
Naslov: Mechanistic study of photoinduced intramolecular H-abstraction in endo- and exo- protoadamantylphthalimides
Izvornik: Central European Conference on Photochemistry (CECP 2012) : abstracts
Skup: Central European Conference on Photochemistry
Mjesto i datum: Bad Hofgastein, Austrija, 05.-09.02.2012.
Ključne riječi: H-abstraction; exo-protoadamantyl-phthalimides; endo-protoadamantyl-phthalimides
Sažetak:
N-Alkylphthalimide derivatives, similar to simple ketones, undergo photoinduced H-abstraction reactions [1]. Particularly interesting are the intramolecular H-abstractions since they give rise to aza-heterocycles, important pharmacophores. Recently we reported on photoinduced intramolecular H-abstractions on a series of adamantyl-phthalimides. We found examples that undergo photoinitiated domino H-abstractions giving complex molecular structures. The photochemical reactivity was investigated in the solid state and in solution, and the mechanism of the reaction elucidated by transient spectroscopy [2]. Herein we report on investigation of photoinduced H-abstractions in a series of protoadamantyl-phthalimides. Two rigid protoadamantyl-phthalimides, exo-1 and endo-1 [3], were strategically prepared to investigate the influence of the molecular structure on the photochemical reactivity. Irradiation of exo-1 gave products 2 and 3, formed by γ-, and ε-H abstraction, respectively. On the other hand, photochemistry of endo-1 is regioselective, giving only product of δ-abstraction. The mechanism of the reaction was investigated by laser flash photolysis. Different reactivity of diastereomers 1 is reflected to different triplet excited state lifetimes.
Vrsta sudjelovanja: Poster
Vrsta prezentacije u zborniku: Sažetak
Vrsta recenzije: Nema recenziju
Projekt / tema: 098-0982933-2911, 02.05/25
Izvorni jezik: ENG
Kategorija: Znanstveni
Znanstvena područja:
Kemija
Upisao u CROSBI: eluksa@irb.hr (eluksa@irb.hr), 21. Vel. 2012. u 11:10 sati



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