The photodecarboxylative addition of carboxylates to phthalimides: scope and limitations

Oelgemöller, Michael, Cygon, Peter, Lex, Johann, and Griesbeck, Axel G. (2003) The photodecarboxylative addition of carboxylates to phthalimides: scope and limitations. Heterocycles, 59 (2). pp. 669-684.

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Abstract

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.

Item ID: 10158
Item Type: Article (Refereed Research - C1)
Keywords: phthalimide; carboxylate; alkylation; photodecarboxylation; photochemistry
ISSN: 1881-0942
Date Deposited: 12 Apr 2010 00:58
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
Citation Count from Web of Science Web of Science 19
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