6279-86-3 Triethyl Methanetricarboxylate
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Methanetricarboxylates have been used as "blocked" malonic esters, restricting reaction with alkyl halides to monoalkylation. The unwanted carboxyl group can be removed by treatment with Na alkoxide, LDA or BCl3: J. Org. Chem., 44, 3492 (1979). Adds to Michael acceptors under phase-transfer conditions, providing a useful 2-carbon chain extension method: Synthesis, 1125 (1990).The tricarboxylate also undergoes free-radical addition to the terminal position of alkenes: Angew. Chem. Int. Ed., 5, 586 (1966). Arylation with electron-rich aromatics is promoted by Mn(III): Synthesis, 567 (1991).
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