A. Kawachi et K. Tamao, Synthesis, structures, and reactions of nitrogen, oxygen, and sulfur-functionalized silyl anions, J SYN ORG J, 59(9), 2001, pp. 892-903
Several types of nitrogen-, oxygen-, and sulfur-functionalized silyllithium
s have been prepared as the first members of stable and/or well-characteriz
able functionalized silyl anions. These functionalized silyllithiums can be
obtained mainly by tin-lithium exchange reaction of the corresponding sily
lstannanes with butyllithium and/or by reaction of the corresponding chloro
silanes with lithium. Described herein are also the general aspects of (1)
high stability of [(amino) silyl]lithiums, (2) low stability of [(alkoxy)si
lyl]lithiums, behaving as silylenoid species, (3) low stability of [(arylth
io)silyl]lithiums, affording silylenes, (4) structure analyses of the [(ami
no) silyl]lithiums in solution and in the solid state, (5) [2,3]-sila-Witti
g rearrangement and cyclopropanation reaction of [(allyloxy)silyl]lithiums
and the chirality transfer during these reactions, (6) functionalized oligo
silane synthesis using [ (amino) silyl] lithiums, and (7) synthetic applica
tion of (aminosilyl) lithiums as a hydroxy anion equivalent by a combinatio
n with the oxidative cleavage of the Si-C bonds.