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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.
These possibilities have been used to account for the fact that, for certain substrates like α-tetralone, the group that migrates can sometimes change, depending on the conditions used, to deliver either of the two possible amides. [8] Two proposed reaction mechanisms for the amide formation from a ketone via Schmidt reaction
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.
The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion (2), also called the Vilsmeier reagent. The initial product is an iminium ion (4b), which is hydrolyzed to the corresponding ketone or aldehyde during workup. [7] The Vilsmeier–Haack reaction
Weerman degradation, also named Weerman reaction, is a name reaction in organic chemistry.It is named after Rudolf Adrian Weerman, who discovered it in 1910. [1] In general, it is an organic reaction in carbohydrate chemistry in which amides are degraded by sodium hypochlorite, forming an aldehyde with one less carbon. [2]
Arndt–Eistert reaction is a series of chemical reactions designed to convert a carboxylic acid to a higher carboxylic acid homologue (i.e. contains one additional carbon atom) Kowalski ester homologation, an alternative to the Arndt-Eistert synthesis. Has been used to convert β-amino esters from α-amino esters through an ynolate ...
The Shapiro reaction or tosylhydrazone decomposition is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate hydrazone in the presence of 2 equivalents of organolithium reagent. [1] [2] [3] The reaction was discovered by Robert H. Shapiro in 1967. [4]
The Wittig reagents generally tolerate carbonyl compounds containing several kinds of functional groups such as OH, OR, nitroarenes, epoxides, and sometimes esters and amides. [13] Even ketone, aldehyde, and nitrile groups can be present if conjugated with the ylide — these are the stabilised ylides mentioned above.