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Issue 4, 2011
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Photoinduced decarboxylation of 3-(N-phthalimido)adamantane-1-carboxylic acid and radical addition to electron deficient alkenes

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Abstract

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.

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

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Publication details

The article was received on 24 Nov 2010, accepted on 06 Jan 2011 and first published on 25 Jan 2011


Article type: Paper
DOI: 10.1039/C0PP00357C
Citation: Photochem. Photobiol. Sci., 2011,10, 610-617

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

    M. Horvat, K. Mlinarić-Majerski, A. G. Griesbeck and N. Basarić, Photochem. Photobiol. Sci., 2011, 10, 610
    DOI: 10.1039/C0PP00357C

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