Propanedioic acids, esters carbon acidity

PEG 300 ethyl-2-cyano-3,3-diphenylacrylate (2-ethylhexyl)-2-cyano-3,3-diphenylacrylate N-(2-ethoxyphenyl)-N -(2-ethylphenyl)oxamide propanedioic acid, j(4-methoxyphenyl)-methylene]-dimethyl ester Screener carbon black, titanium dioxide, zinc oxide Acid scavenger hydrotalcite ... 

In Section 23-2 two reactions of /3-tlicarbonyl compoiiiiJs arc presented. The (irst is alkylation of the readily deprotonated "carbon in the middle." The second pertains to /3-dicarbonyi compounds where at least one of the carbonyl groups is an ester. Ester hydrolysis leads to a carboxylic acid that readily loses COi (decarboxylation). When this sequence is carried out on a /3-ketocster, the result is a ketone. When carried out on a diester of propanedioic (malonic) acid, the result is a carboxylic acid. In each case, groups attached in the preliminary alkylation slep(s) wind up in the product. 

Malonic ester synthesis (Section 18.7) A reaction in which the a-hydrogen of diethyl propanedioate (diethyl malonate, also called malonic ester ) is removed, creating a resonance-stabilized anion which can serve as a nucleophile in an 5 2 reaction. The a-carbon can be substituted twice the ester functionalities can be converted into a carboxylic acid which, after decarboxylation, will yield a substituted ketone. 

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