Proton and 13C NMR studies of the title compound, 4, in THF-8 and toluene-8 show it to exist as an equilibrium mixture of endo-silyi and exo-silyl species in which lithium is tridentately complexed to the pendant ligand and the whole effects were observed for 1 complexed to pentamethyldi-ethylenetriamine11 and for (1,1,3,3-tetramethylallyl)lithium• TMEDA.15 The nature of this reorientation process is not yet clear.This paper deals with the behavior of the title compound, 4, a (silylallyl)lithium with a pendant potential ligand, [bis(2methoxyethyl)amino] methyl, attached to silicon, first reported by Chan and Horvath.16 These authors proposed that if 4 assumes the fully folded, internally complexed conformation, then perhaps proximity of Li+ to C, would favor reaction of electrophiles at C, instead of the usual result for 1, exclusive reaction at C3.
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