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Paper | Special issue | Vol 59, No. 2, 2003, pp.669-684
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S77
The Photodecarboxylative Addition of Carboxylates to Phthalimides: Scope and Limitations

Michael Oelgemöller, Peter Cygon, Johann Lex, and Axel G. Griesbeck*

*Institute of Organic Chemistry, University of Cologne, Greinstrasse 4, D-50939 Köln, Germany


Intermolecular photoinduced decarboxylative additions of a series of alkylcarboxylates to N-substituted phthalimides gave the corresponding hydroxy-phthalimidines in moderate to high yields of 39-89%. The potassium salt of 1- adamantanecarboxylic acid predominately underwent simple decarboxylation when irradiated in the presence of N-methylphthalimide. In case of phthalimides carrying suitable leaving groups within the N-side chain, decarboxylation, retro-Aldol cleavage or decarbonylation preceded the intermolecular addition step.