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Nucleophile- or Light-Induced Synthesis of 3-Substituted Phthalides from 2-Formylarylketones

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journal contribution
posted on 04.05.2012, 00:00 by Dario C. Gerbino, Daniel Augner, Nikolay Slavov, Hans-Günther Schmalz
The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro–Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm).