Naslov
Mechanistic study of photoinduced intramolecular H-abstraction in endo- and exo- protoadamantylphthalimides

Autori
Cindro, Nikola ; Mlinarić-Majerski, Kata ; Halasz, Ivan ; Griesbeck ; Axel G. ; Basarić, Nikola

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

Izvornik
Central European Conference on Photochemistry (CECP 2012) : abstracts / - , 2012, 110-110

Skup
Central European Conference on Photochemistry

Mjesto i datum
Bad Hofgastein, Austrija, 05.02.2012. - 09.02.2012

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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