Eschenmoser's salt
Names | |
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IUPAC name
Dimethylmethylideneammonium iodide | |
Identifiers | |
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3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.046.968 |
PubChem CID |
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Properties | |
C3H8NI | |
Molar mass | 185.01 g/mol |
Appearance | colorless hygroscopic crystals |
Melting point | 116 °C (241 °F; 389 K) |
decomposes | |
Hazards | |
R-phrases (outdated) | R36/37/38 |
S-phrases (outdated) | S26 S36 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
Infobox references | |
Eschenmoser's salt, dimethylmethylideneammonium iodide, is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)2.[1][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[3] after whom the reagent is named.
Analogous salts, dimethylmethylideneammonium chloride (Böhme's salt[1], after Horst Böhme) and trifluoroacetate, have similar properities and applications.[1]
References
- 1 2 3 E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.rd346
- ↑ Horst Böhme; Eberhard Mundlos; Otto-Erich Herboth (1957). "Über Darstellung und Eigenschaften α-Halogenierter Amine". Chemische Berichte. 90 (9): 2003–2008. doi:10.1002/cber.19570900942.
- ↑ Jakob Schreiber; Hans Maag; Naoto Hashimoto; Albert Eschenmoser (1971). "Dimethyl(methylene)ammonium Iodide". Angewandte Chemie International Edition in English. 10 (5): 330–331. doi:10.1002/anie.197103301.
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