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Formation of mixed aryl-, alkyl-lithium aggregates in the heteroatom assisted lithiation of a,a'-dialkyl substituted 1,3-bis[(dimethylamino)methyl]benzene

By G. van Koten, J.G. Donkervoort, J.L. Vicario, E. Rijnberg, J.T.B.H. Jastrzebski, H. Kooijman and A.L. Spek


The heteroatom assisted lithiation of 1, 3-bis[1-(dimethylamino)ethyl]benzene with n-BuLi afforded 2,6-bis[1-(dimethylamino)ethyl]phenyllithium. An X-ray crystal structure determination revealed a dimeric aggregate in which the four benzylic chiral centers are identical, pointing to stereoselective crystallization. In contrast, reaction of 1,3-bis[1-(dimethylamino)propyl]benzene with n-BuLi afforded a dimeric aggregate comprising the parent lithiated compound and n-BuLi in a 1:1 molar ratio. The four Li atoms and the four bridging carbon atoms are arranged in a unique ladder-type C-Li2-C2'-Li2-C framework

Topics: Scheikunde
Year: 1998
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