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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 16
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Original Articles

N-Lithio-N,N′,N″,N″-tetramethyldiethylenetriamine and N′-Lithio-N,N,N″,N″-tetramethyldiethylenetriamine; Oxidative Coupling of Aminomethyllithium Derivatives

, &
Pages 2257-2261 | Received 31 Jan 1994, Published online: 23 Sep 2006
 

Abstract

N-lithio-N,N′,N″,N″-tetramethyldiethylenetriamine (I-Li) is formed from 2,5,8,11-tetramethyl-2,5,8,11-tetraazadodecane (III) or from 2,5,8,11,14,17-hexamethyl-2,5,8,11,14,17-hexaazaoctadecane (IV) with n-BuLi or sec-BuLi, respectively, its isomer N′ -lithio-N,N,N″,N″,-tetramethyldiethylene-triamine (II-Li) from tris(2-dimethylaminoethyl)amine (V) with n-BuLi. IV results from treatment of N-lithiomethyl-N,N′,N″,N″-tetramethyldiethylenetriamine (PMDTA-Li) with 1,2-dibromoethane.

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