Eschenmoser's_salt
Eschenmoser's salt
Ionic compound with the formula [(H3C–)2N–CH2]I
In organic chemistry, Eschenmoser's salt (named for Albert Eschenmoser) is the ionic, organic compound [(CH3)2NCH2]I. It is the iodide salt of the dimethylaminomethylene cation [(CH3)2NCH2]+.
The dimethylaminomethylene cation is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)2.[1][2] Enolates, silyl enol ethers, and even more acidic ketones undergo efficient dimethylaminomethylation. Once prepared, such tertiary amines can be further methylated and then subjected to base-induced elimination to afford methylidenated ketones. The salt was first prepared by the group of Albert Eschenmoser[3] after whom the reagent is named.
![{\displaystyle {\ce {[(CH3)3N-CH2I]I -> [(CH3)2NCH2]I + CH3I}}}](http://wikimedia.org/api/rest_v1/media/math/render/svg/1ef55f57992c279d24cd25843b851778be0d4078)
![{\displaystyle {\ce {[(CH3)2N]2CH2 + (CH3)3SiI -> [(CH3)2NCH2]I + (CH3)3SiN(CH3)2}}}](http://wikimedia.org/api/rest_v1/media/math/render/svg/a79dec87a81d283c410a7c32e737efdfa9dc2341)
