Naslov
Photoinduced decarboxylation of 3-(N-phthalimido)adamantane-1-carboxylic acid and radical addition to electron deficient alkenes

Autori
Horvat, Margareta ; Mlinarić-Majerski, Kata ; Griesbeck, Axel G. ; Basarić, Nikola

Izvornik
Photochemical & photobiological sciences (1474-905X) 10 (2011), 4; 610-617

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

Ključne riječi
adamantane amino acids; photodecarboxylation; phthalimides; radical addition to alkenes; reaction mechanism

Sažetak
Direct and sensitized excitation of 3-(N-phthalimido)adamantane-1-carboxylic acid (1) leads to the population of the triplet state that in the presence of a base, decarboxylates, giving N-(1-adamantyl)phthalimide (2) cleanly and efficiently (Φ = 0.11). The radical initially formed by decarboxylation adds regiospecifically to electron deficient alkenes, whereas radical addition was not observed for electron rich alkenes. The radical addition can also be applied to molecules not bearing adamantanes wherein the electron donor (carboxylate) and the acceptor (phthalimide) are separated by a rigid spacer. The photodecarboxylation induced radical addition of phthalimide derivative 1 to alkenes takes place in good to excellent yields and represents a mild and efficient method for C-C bond formation.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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