Eschenmoser's salt

In organic chemistry, Eschenmoser's salt (named for Albert Eschenmoser) is the ionic, organic compound [(CH3)2NCH2]I.

The dimethylaminomethylene cation is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)2.

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.

Pyrolysis of iodomethyltrimethylammonium iodide affords the desired salt:[3] An alternative route starts with bis(dimethylamino)methane: Other salts of the dimethylaminomethylene cation:

Eschenmoser's salt
Eschenmoser's salt