A lone pair from the nitrogen forms a pi-bond to expel the positively charged leaving group, and also causes the nitrogen to harbor a synthesis charge.
The synthesis proceeds through an intramolecular heteroatom Peterson olefination, ultimately resulting in an elimination reaction which expels a TMSO group and forms a pi-bond in the five-membered ring at the nitrogen atom. Then, keto-enol tautomerism occurs, resulting in the desired product. When this occurs, the pi-bond of the synthesis is converted into a lone paircreating a negatively charged oxygen.
After these initial steps, strong base is no longer required and hydrolysis must occur. Pictures, videos, biodata, and files relating to Madelung synthesis are also acceptable encyclopedic sources.
The synthesis proceeds through an intramolecular heteroatom Peterson olefination, ultimately resulting in an elimination reaction which expels a TMSO group and forms a pi-bond in the five-membered ring at the nitrogen atom. The negatively charged nitrogen is protonated to regain its neutral charge, and the oxygen is protonated twice to harbor a positive charge in order to become a good leaving group.
A detailed reaction mechanism for the Madelung synthesis follows. This allows the pi-bond formed by nitrogen in the preceding step to be converted back into a lone pair on nitrogen to restore nitrogen's neutral charge.
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