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Synthetic routes for the following dendrimers are described: Si[CH 2 CH 2 Si(Me) 2 CH 2 -3,5-(MeO) 2 -C 6 H 3 ] 4 (2) and Si[CH 2 CH 2 Si(Me) 2 -2,4-(MeO) 2 -C 6 H 3 ] 4 (4). The crystal structures of these dendrimers have been determined by single crystal X-ray diffraction. One of the dendrimers (2) shows crystallographic S 4 -symmetry and intramolecular C-H...O bonding, whereas the other (4) shows crystallographic C 2 -symmetry and is imbedded in a zipper-like network of intermolecular C-H...O bonds. Direct lithiation of these dendrimers with n-BuLi in Et 2 O yields complete and selective lithiation in the aryl ring between the methoxy substituents. However, dendrimer 2 is also partially lithiated in the benzylic group. For the solid state structure of such lithiated dendrimers, a diamond-type assembly is predicted.
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