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Studies on the reaction of 1,2-dicarbonyl compounds with dimethyl 3-ketoglutarate. Steric and electronic effects

✍ Scribed by G. Kubiak; J.M. Cook; U. Weiss

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
285 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

The steric and electronic influences of.subs.ituen 'j attached to he arbonyl system on the success of the reaction o 1 1,2-$lketones with $imethyl 3-ketoglutarate 2. have been examined.

It is clear from the reaction of 2 with benzil, thienil. furil. and phenanthrenequinone 1. respectively, coupled with 13c NMR spectroscopy of the reaction intermediates, that steric effects play a major role in the overall success of the reaction to provide 4. This is analogous to the situation observed earlier with 1,2-diketones, R-CO-CO-R, where R represented an aliphatic or alicyclic group.

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