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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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 Type:||Article (Refereed Research - C1)|
|Keywords:||phthalimide; carboxylate; alkylation; photodecarboxylation; photochemistry|
|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||