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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

Horvat, Margareta ; Mlinarić-Majerski, Kata ; Griesbeck, Axel G. ; Basarić, Nikola Photoinduced decarboxylation of 3-(N-phthalimido)adamantane-1-carboxylic acid and radical addition to electron deficient alkenes // Photochemical & photobiological sciences, 10 (2011), 4; 610-617. doi: 10.1039/c0pp00357c

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

Povezanost rada

Kemija

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