N. Rot et F. Bickelhaupt, FORMATION OF 1,3,5-TRILITHIOBENZENE AND ITS CONVERSION TO THE CORRESPONDING MAGNESIUM, MERCURY AND TIN DERIVATIVES, Organometallics, 16(23), 1997, pp. 5027-5031
Whereas the halogen-metal exchange approach from 1,3,5-tribromobenzene
(3) to 1,3,5-trilithiobenzene (1) was unsuccessful, 1 was synthesized
in high yield (about 80%) by reaction of 3 with LiDBB (lithium 4,4'-d
i-tert-butylbiphenyl). Compound 1 was used as the starting material fo
r the preparation of other symmetrical trimetalated benzenes, 1,3,5-C6
H3(MgBr)(3) (20), 1,3,5-C6H3(SnMe3)(3) (23), and 1,3,5-C6H3(HgBr)(3) (
26), by reaction with the corresponding metal halides.