Eisleb alkylation
The Eisleb alkylation is a name reaction in organic chemistry, which was first introduced in 1941 by the German chemist Otto Eisleb (1887–1948) and named after him.
Overview reaction
This reaction is an alkylation of compounds with active hydrogen using an alkyl halide and treatment with sodium amide. CH-acidic compounds are u. a. Deoxybenzoin, diphenylmethane , phenylacetonitrile , fluorene , benzylphenylsulphone and 2-pyridylacetonitrile.
Reaction mechanism
In this reaction, the sodium amide first abstracts a proton, which creates a carbanion . In this step, ammonia is produced from the amide. A nucleophilic attack on the positively polarized alkyl radical of the alkyl halide can then take place. The sodium halide can be removed and the alkylated product remains.
Sample reaction
Eisleb describes the reaction itself for the dialkylation of benzyl cyanide using sodium amide with the formation of heterocycles. This can be done with connections from the group of the lottery :
application
This reaction is used to alkylate compounds with active hydrogen atoms.
Individual evidence
- ↑ a b c d Zerong Wang: Eisleb alkylation . In: Comprehensive Organic Name Reactions and Reagents . Wiley, 2010, ISBN 978-0-470-63885-9 , pp. 974-976 , doi : 10.1002 / 9780470638859.conrr211 .
- ↑ Otto Eisleb: New syntheses using sodium amide . In: Reports of the German Chemical Society (A and B Series) . tape 74 , no. 8 , August 6, 1941, p. 1433-1450 , doi : 10.1002 / cber.19410740814 .