Journal of the Chemical Society, Dalton Transactions p. 2723 - 2728 (1988)
Update date:2022-08-04
Topics:
Van Westrenen, Jeroen
Peters, Joop A.
Kieboom, Antonius P. G.
Van Bekkum, Herman
The lanthanum(III)-catalysed addition of glycolate to maleate to yield carboxymethoxysuccinate(3-) (cmos) is described. It is shown that the reaction only proceeds above pH 6, indicating the formation of di-ionised glycolate as a pre-equilibrium for the rate-limiting step, i.e. the addition of the CH2-O- to the olefinic bond. Due to strong complexation of LaIII by the product cmos, the reaction requires one LaIII ion per two cmos formed. The inhibitory effects of non-reacting strong chelators such as ethylenediaminetetra-acetate, nitrilotriacetate, and 2,6-pyridinedicarboxylate indicate the formation of mixed-ligand complexes leading to the addition reaction. This has been confirmed by GdIII-induced 13C relaxation rate enhancements, and DyIII-induced 17O shift measurements.
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