1,1-Cyclobutane dicarboxylic acid

1,1-Cyclobutane dicarboxylic acid is an organic compound. It has the chemical formula C4H6(COOH)2. Its conjugate base is 1,1-cyclobutane dicarboxylate, C4H6(COO)2−2. This anion is used as a ligand in some platins, a type of anticancer drug.

Preparation

As an alkylated derivative of malonic acid, 1,1-cyclobutane dicarboxylate esters can be made using the malonic ester synthesis with 1,3-dibromopropane.[1]

A strong base like sodium ethoxide reacts with diethyl malonate, removing a hydrogen atom from the activated methylene bridge to make an enolate reaction intermediate. The enolate is a nucleophile that attacks one end of the dibromide in an SN2 reaction. More base then removes the other hydrogen atom from the activated methylene bridge, making another enolate, then an intramolecular SN2 reaction with the other bromide closes the loop to make the cyclobutane dicarboxylate ester.

Alkaline hydrolysis gives the dicarboxylate, which is re-acidified to the acid.[1]

References

  1. 1 2 G. B. Heisig and F. H. Stodola (1943). "1,1-Cyclobutanedicarboxylic acid and cyclobutanecarboxylic acid". Organic Syntheses. 23: 16.
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