Direct mono-N-alkylation of amines in ionic liquids: chemoselectivity and reactivityThis work was presented at the Green Solvents for Catalysis Meeting, held in Bruschal, Germany, 13–16 October 2002

Autor:	Daniela Pieraccini, Cinzia Chiappe
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Iodide Alkylation Pollution chemistry.chemical_compound Caesium hydroxide chemistry Bromide Ionic liquid Environmental Chemistry Organic chemistry Reactivity (chemistry) Chemoselectivity Alkyl
Zdroj:	Green Chemistry. 5:193-197
ISSN:	1463-9270 1463-9262
DOI:	10.1039/b211340f
Popis:	A simple method for the N-alkylation of primary amines was developed using ionic liquids as solvent in order to prepare secondary amines selectively. In ionic liquids overalkylation of the initially produced secondary amines is in general markedly reduced. Various amines, alkyl halides and sulfonates were examined. The observed selectivities between mono- and dialkylation are typically on the order of 9∶1, or higher. Only in the cases of allyl or benzyl bromides does the reaction give the corresponding tertiary amines exclusively. The relative nucleofugality of chloride, bromide, iodide and tosylate with several primary amines was also evaluated, as well as the effect of caesium hydroxide.
Databáze:	OpenAIRE
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