o-(Chlorodimethylsilyl)-N,N-dimethylaniline was prepared and characterized by NMR and
X-ray crystallography. Reaction of this reagent with K2C8H8 gives selectively 1,4-bis[(o-dimethylsilyl)-N,N-dimethylaniline]cycloocta-2,5,7-triene. Further reaction with 2 equiv
n-BuLi affords a new functionalized cyclooctatetraenide, Li2-1,4-R2C8H6 (R = o
-(dimethylsilyl)-N,N-dimethylaniline). The new ligand is a useful starting material for the preparation of
organolanthanide sandwich complexes, [Li(diglyme)2]+[Ln(1,4-R2C8H6)2]- (Ln = Nd, Sm).
These metal complexes were characterized by NMR and X-ray crystallography. They are
the first examples of structurally characterized cyclooctatetraene complexes with a donor
functionality attached to the eight-membered ring.