Griesbeck, Axel G., and Oelgemoeller, Michael (2000) Decarboxylative photoadditions of heteroatom-substituted carboxylates to phthalimides. Synlett, 2000 (1). pp. 71-72.

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Abstract

a-Thioalkyl and a-oxoalkyl-substituted potassium carboxylates efficiently decarboxylate in the presence of electronically excited phthalimides. Radical coupling and reduction products result from secondary steps. In contrast, b-thioalkyl-substituted carboxylates are unreactive under the reaction conditions whereas b-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 b-thioalkyl-substituted carboxylates, the thioether radical cation serves as hole trap and prevents the carboxylate of oxidative cleavage.

Item ID:	29977
Item Type:	Article (Research - C1)
ISSN:	1437-2096
Keywords:	photodecarboxylation, phthalimides, electron transfer, carbonyl addition
Funders:	Deutsche Forschungsgemeinschaft (DFG), Fonds der Chemischen Industrie
Projects and Grants:	DFG - GR 881/7-3
Date Deposited:	16 Jul 2014 05:01
FoR Codes:	03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 60% 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 40%
SEO Codes:	97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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