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The mechanism of thermal eliminations. Part XXVIII [1]: Thermal decomposition of benzoylformic acid

✍ Scribed by Roger Taylor

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
195 KB
Volume
23
Category
Article
ISSN
0538-8066

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✦ Synopsis

The thermal decomposition of benzoylformic acid into carbon dioxide and benzaldehyde is a unimolecular first-order reaction which takes place according to the rate equation log k = 15.3-42,500/4.575 K. At 600 K the reaction takes place 18 times faster than the corresponding decomposition of pyruvic acid into carbon dioxide and acetaldehyde. This is consistent with the 4-center process proposed previously for pyruvic acid, in which a partial negative charge develops on the carbon of the a-carbonyl group in the transition state. Benzoylformic acid is considerably less reactive towards thermal elimination than is oxalic acid, which also accords with the proposed mechanism.

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