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

M Horvat, K Mlinarić-Majerski, AG Griesbeck…

Index: Horvat, Margareta; Mlinaric-Majerski, Kata; Griesbeck, Axel G.; Basaric, Nikola Photochemical and Photobiological Sciences, 2011 , vol. 10, # 4 p. 610 - 617

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Citation Number: 19

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 ...