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The classic example is the conversion of glucose to arabinose as shown below. The reaction is named after the German chemist Alfred Wohl (1863–1939). The Wohl degradation. Let's say we have a kiliani-fischer synthesis, it basically removes the row of the C2 carbon, it shortens the carbon chain by one carbon.
Base abstraction of the remaining amide proton gives a bromoamide anion. The bromoamide anion rearranges as the R group attached to the carbonyl carbon migrates to nitrogen at the same time the bromide ion leaves, giving an isocyanate. The isocyanate adds water in a nucleophilic addition step to yield a carbamic acid (aka urethane).
The reaction mechanism involves the acylation and activation of the acid 1 to the mixed anhydride 3. The amide will serve as a nucleophile for the cyclization forming the azlactone 4. Deprotonation and acylation of the azlactone forms the key carbon-carbon bond. Subsequent ring-opening of 6 and decarboxylation give the final keto-amide product ...
In organic chemistry, the Arndt–Eistert reaction is the conversion of a carboxylic acid to its homologue. It is named for the German chemists Fritz Arndt (1885–1969) and Bernd Eistert (1902–1978). The method entails treating an acid chlorides with diazomethane. It is a popular method of producing β-amino acids from α-amino acids. [1]
Nahm and Weinreb also reported the synthesis of aldehydes by reduction of the amide with an excess of lithium aluminum hydride (see amide reduction). The Weinreb–Nahm ketone synthesis. The major advantage of this method over addition of organometallic reagents to more typical acyl compounds is that it avoids the common problem of over-addition.
Attack by water converts 6 to protonated imidic acid 7, which undergoes loss of proton to arrive at the imidic acid tautomer of the final amide. In an alternative mechanism, the migration occurs at 9, directly after protonation of intermediate 3, in a manner similar to the Baeyer–Villiger oxidation to give protonated amide 10. Loss of a ...
Some amides can be reduced to aldehydes in the Sonn-Müller method, but most routes to aldehydes involve a well-chosen organometallic reductant. Lithium aluminum hydride reduces an excess of N,N-disubstituted amides to an aldehyde: [citation needed] R(CO)NRR' + LiAlH 4 → RCHO + HNRR' With further reduction the alcohol is obtained.
And below -CH2OH will convert to -CHO group through the reduction of iron from its +3 state to +2 state, thus forming D-Arabinose. Hexoses converted to pentoses by Ruff degradation This reaction was an important tool used by Emil Fischer to show that D-Glucose and D-Mannose each formed the same product upon Ruff degradation (D-Arabinose ...
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