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Synlett 2000; 2000(1): 71-72
DOI: 10.1055/s-2000-6443
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Decarboxylative Photoadditions of Heteroatom-substituted Carboxylates to Phthalimides

Axel G. Griesbeck* , Michael Oelgemöller
  • *Department of Organic Chemistry, Universität zu Köln, Greinstr. 4, D-50939 Köln, Germany; Fax +49 2 21 4 70 50 57; E-mail: griesbeck@uni-koeln.de
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Publication Date:
31 December 2000 (online)

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α-Thioalkyl and α-oxoalkyl-substituted potassium carboxylates efficiently decarboxylate in the presence of electronically excited phthalimides. Radical coupling and reduction products result from secondary steps. In contrast, β-thioalkyl-substituted carboxylates are unreactive under the reaction conditions whereas β-oxoalkyl-substituted carboxylates react quantitatively. This behaviour is rationalized by assuming primary photoinduced electron transfer with sulfur oxidation, respectively, and no oxidation of the ether oxygen. In β-thioalkyl-substituted carboxylates, the thioether radical cation serves as hole trap and prevents the carboxylate of oxidative cleavage.

photodecarboxylation - phthalimides - electron transfer - carbonyl addition

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