Lithiation of TMEDA and its higher homologous TEEDA: understanding observed alpha- and beta-deprotonation.
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.
Gessner
Viktoria H
VH
Anorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Str. 6, 44227 Dortmund, Germany.
Strohmann
Carsten
C