Eschenmoser's salt

Eschenmoser's salt

Chembox new
Name = Eschenmoser's salt
ImageFile = Eschenmosersalz.png ImageName = Eschenmoser's salt
IUPACName = Dimethylmethylideneammonium iodide
Section1 = Chembox Identifiers
SMILES = C [N+] (C)=C. [I-]
CASOther = [30354-18-8] (Chloride)
[33797-51-2] (Iodide)
RTECS =
Section2 = Chembox Properties
Formula = C3H8NI
MolarMass = 185.01 g/mol
Appearance = colorless hygroscopic crystals
Solubility = decomp.
MeltingPt = 116 °C
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards =
FlashPt =
RPhrases = 36/37/38
SPhrases = 26-36
Section8 = Chembox Related
OtherCpds =

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. [cite journal
author = Jakob Schreiber, Hans Maag, Naoto Hashimoto, Albert Eschenmoser
title = Dimethyl(methylene)ammonium Iodide
journal = Angewandte Chemie International Edition in English
volume = 10
issue = 5
year = 1971
pages = 330–331
doi = 10.1002/anie.197103301]

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.


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