Naslov
Photo-initiated Domino Reactions of Adamantyl-phthalimides: Product Study and Investigation by Time-resolved Spectroscopy

Autori
Basarić, Nikola ; Horvat, Margareta ; Mlinarić-Majerski, Kata ; Görner, Helmut ; Warzecha, Klaus-Dieter ; Neudörfl, Jörg ; G. Griesbeck, Axel

Izvornik
Gordon Research Conference on Photochemistry, Bryant University, Smithfield, RI, U.S.A.

Vrsta, podvrsta
Ostale vrste radova, ostalo

Godina
2009

Ključne riječi
Phtalimides; H-abstraction; electron transfer

Sažetak
Within the framework of developing sustainable technologies, chemists are obliged to find new environment-friendly production procedures. Domino reactions [1] initiated by photons appear to be particularly interesting in the context of green chemistry. However, not many examples of domino reactions initiated by photons are known. Recently we reported a novel photoinitiated domino process of N-(1-adamantyl)phthalimide (1) that gives rise to a methanoadamantane-benzazepine derivative via two consecutive photochemical hydrogen abstractions. [2] Herein we report an investigation of factors which determine the photochemical reactivity on the series of six N-(adamantyl)phthalimides, giving rise to the thermal and the photochemical domino processes. The investigated phthalimides undergo photochemical reactions on direct and sensitized irradiation and give rise to products that were isolated and characterized. The lowest triplet state of phthalimides was characterized in several solvents upon direct and acetone sensitized excitation. Electrochemical measurements showed that intramolecular electron transfer from the adamantyl group to the lowest triplet state of the phthalimides is not feasible. The formation of products can be explained by intramolecular H-abstraction from the (alkyl)adamantane to the excited phthalimide, either from the excited singlet state or a hidden upper excited triplet state.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA