Photoinduced decarboxylation of 3-(N-phthalimido)adamantane-1-carboxylic acid and radical addition to electron deficient alkenes (CROSBI ID 168475)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Horvat, Margareta ; Mlinarić-Majerski, Kata ; Griesbeck, Axel G. ; Basarić, Nikola
engleski
Photoinduced decarboxylation of 3-(N-phthalimido)adamantane-1-carboxylic acid and radical addition to electron deficient alkenes
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.
adamantane amino acids; photodecarboxylation; phthalimides; radical addition to alkenes; reaction mechanism
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Podaci o izdanju
10 (4)
2011.
610-617
objavljeno
1474-905X
10.1039/c0pp00357c