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- W2950552617 abstract "The Weiss–Cook condensation of dimethyl 2,3-dioxobutanedioate with two equivalents of dimethyl 3-oxoglutarate in aqueous bicarbonate produces an abnormal product, pentamethyl cis-3-(carbomethoxymethyl)-3,7-dihydroxy-2-oxabicyclo-[3.3.0]oct-7-ene-1,4,5,6,8-pentacarboxylate 7, whose structure has been determined by X-ray crystallography. Rrapcho decarbomethoxylation (sodium chloride, aqueous dimethyl sulfoxide, 140 °C) of this compound produces dimethyl cis-3,7-dioxobi-cyclo[3.3.0]octane-1,5-dicarboxylate 4 in quantitative yield. These results suggest that compound 7 may be the product of a kinetically controlled reaction pathway involving 4-hydroxypent-2-en-1-one intermediate 5. Heating of 7 in dimethyl sulfoxide may have promoted thermodynamic equilibration to a Weiss–Cook product, which then decarbomethoxylated to produce 4." @default.
- W2950552617 created "2019-06-27" @default.
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- W2950552617 date "2010-08-18" @default.
- W2950552617 modified "2023-09-26" @default.
- W2950552617 title "ChemInform Abstract: Unusual Weiss-Cook Condensation of Dimethyl 2,3-Dioxobutanedioate and Dimethyl 3-Oxoglutarate." @default.
- W2950552617 cites W1995552133 @default.
- W2950552617 doi "https://doi.org/10.1002/chin.199448061" @default.
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