Photoinduced decarboxylation reactions: radical chemistry in water

Griesbeck, Axel G., Kramer, Wolfgang, and Oelgemoeller, Michael (1999) Photoinduced decarboxylation reactions: radical chemistry in water. Green Chemistry, 1. pp. 205-207.

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Abstract

Intramolecular photodecarboxylation reactions of potassium ω-phthalimido carboxylates in water or mixtures of water and organic solvents (acetone, acetonitrile) were investigated using an incoherent XeCl excimer radiation source emitting at 308 nm. Electron transfer induced intermolecular addition of alkyl carboxylates to phthalimides likewise proceeded efficiently under these conditions. The reactions can be performed in multigram (i.e. 10–30 g product) quantities using easily available substrates such as glutamic acid (for the synthesis of 3), leucine (for 8, 9) or simple alkyl carboxylates (for 11). The advantages of this methodology are: clean and high-yielding reactions, solvent and waste minimization, water-based processes and efficient utilization of photons of defined energy.

Item ID: 29875
Item Type: Article (Research - C1)
ISSN: 1463-9270
Funders: Deutsche Forschungsgemeinschaft (DFG), Fonds der Chemischen Industrie
Projects and Grants: DFG GR 881/7-3
Date Deposited: 21 Mar 2014 22:05
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 40%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030504 Organic Green Chemistry @ 40%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 20%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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