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The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α-hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid. First performed by Justus von Liebig in 1838, [1] it is the first reported example of a rearrangement ...
The decarboxylation of this compound by heat is essential for the psychoactive effect of smoked cannabis, and depends on conversion of the enol to a keto group when the alpha carbon is protonated. Upon heating, Δ9-tetrahydrocannabinolic acid decarboxylates to give the psychoactive compound Δ9- Tetrahydrocannabinol . [ 13 ]
It is formed by oxidation of TNT and nitric acid with chlorate [2] and with dichromate. [3] Upon heating, 2,4,6-trinitrobenzoic acid undergoes decarboxylation to give 1,3,5-trinitrobenzene. [4] Reduction with tin gives 2,4,6-triaminobenzenoic acid, a precursor to phloroglucinol (1,3,5-trihydroxybenzene). [5]
The carboxylic acid Schmidt reaction starts with acylium ion 1 obtained from protonation and loss of water. Reaction with hydrazoic acid forms the protonated azido ketone 2 , which goes through a rearrangement reaction with the alkyl group R, migrating over the C-N bond with expulsion of nitrogen.
In the absence of metal catalysts, decarbonylation (vs decarboxylation) is rarely observed in organic chemistry. One exception is the decarbonylation of formic acid: H CO OH → CO + H 2 O. The reaction is induced by sulfuric acid, which functions as both a catalyst and a dehydrating agent.
Under these conditions the condensation is accompanied by decarboxylation. [4] For example, the reaction of acrolein and malonic acid in pyridine gives trans-2,4-entadienoic acid with one carboxylic acid group and not two. [5] Sorbic acid can be prepared similarly by replacing acrolein with crotonaldehyde. [6]
An example of the Hell–Volhard–Zelinsky reaction can be seen in the preparation of alanine from propionic acid.In the first step, a combination of bromine and phosphorus tribromide is used in the Hell–Volhard–Zelinsky reaction to prepare 2-bromopropionic acid, [3] which in the second step is converted to a racemic mixture of the amino acid product by ammonolysis.
1,3,5-Trinitrobenzene is produced by decarboxylation of 2,4,6-trinitrobenzoic acid. [2] [3] 1,3,5-Trinitrobenzene forms charge-transfer complexes with electron-rich arenes. Reduction of 1,3,5-trinitrobenzene gives 1,3,5-triaminobenzene, a precursor to phloroglucinol. [4]