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. 2008 Nov 5;130(44):14412-3.
doi: 10.1021/ja8058205. Epub 2008 Oct 9.

Lithiation of TMEDA and its higher homologous TEEDA: understanding observed alpha- and beta-deprotonation

Viktoria H Gessner  1 , Carsten Strohmann
Affiliations

Lithiation of TMEDA and its higher homologous TEEDA: understanding observed alpha- and beta-deprotonation

Viktoria H Gessner et al. J Am Chem Soc. .

Abstract

TMEDA and its ethyl-substituted analogue, TEEDA, show a different behavior toward the deprotonation with lithiumalkyls. While TMEDA mainly undergoes alpha-lithiation of its methyl group, TEEDA shows selective beta-lithiation with following elimination of ethene. The crystal structure of the monomeric intermediate of this beta-lithiation, tBuLi.TEEDA, and theoretical studies indicate kinetic favoritism for the beta-lithiation.

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