Eschenmoser's salt
From Wikipedia, the free encyclopedia
| Eschenmoser's salt | |
|---|---|
 |
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| IUPAC name | Dimethylmethylideneammonium iodide |
| Identifiers | |
| CAS number | [30354-18-8] (Chloride) [33797-51-2] (Iodide) |
| SMILES | C[N+](C)=C.[I-] |
| Properties | |
| Molecular formula | C3H8NI |
| Molar mass | 185.01 g/mol |
| Appearance | colorless hygroscopic crystals |
| Melting point |
116 °C |
| Solubility in water | decomp. |
| Hazards | |
| R-phrases | 36/37/38 |
| S-phrases | 26-36 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Eschenmoser's salt, dimethylmethylideneammonium iodide, is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)2. Enolates, enolsilylethers, 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 methylenated ketones. The salt was first prepared by the group of Albert Eschenmoser after whom the reagent is named.[1]
[edit] References
- E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
- H. Böhme, E. Mundlos, O.-E.Herboth, "Über Darstellung und Eigenschaften alpha-Halogenierter Amine" Chemische Berichte 1957, 90, 2003-2008.
- ^ Jakob Schreiber, Hans Maag, Naoto Hashimoto, Albert Eschenmoser (1971). "Dimethyl(methylene)ammonium Iodide". Angewandte Chemie International Edition in English 10 (5): 330–331. doi:.
