77589-54-9Relevant articles and documents
Tetramethyl 3,7-Dihydroxybicyclonona-2,6-diene-2,4,6,8-tetracarboxylate: A Useful Companion to Meerwein's Ester. Topological Analysis of Bicyclononane Synthesis
Bertz, Steven H.
, p. 3585 - 3592 (2007/10/02)
The pH dependence of the condensation of dimethyl 3-oxoglutarate and malondialdehyde to produce 2,6-bis(methoxycarbonyl)phenol and tetramethyl 3,7-dihydroxybicyclonona-2,6-diene-2,4,6,8-tetracarboxylate has been studied in detail: the yield of the former is maximal at pH 4,5, the latter at pH 7.5.The hydrolysis-decarboxylation of the latter provides a convenient route to bicyclononane-3,7-dione.The mechanism proposed for this reaction of malonodialdehyde is also relevant to the chemistry of glyoxal and dimethyl 3-oxoglutarate.The retrosynthetic analysis of the bicyclononane skeleton is considered from a topological perspective.
2,5-Bis(methoxycarbonyl)-4-hydroxycyclopent-2-en-1-one as an Intermediate in Weiss' Glyoxal Reaction. Analogous Chemistry of Malondialdehyde
Bertz, Steven H.,Adams, William O.,Silverton, J. V.
, p. 2828 - 2830 (2007/10/02)
Glyoxal and dimethyl 3-oxoglutarate condense at pH nonane-2,4,6,8-tetracarboxylate.
