Formation of mixed aryl–, alkyl–lithium aggregates in the heteroatom assisted lithiation of α,α′-dialkyl substituted 1,3-bis[(dimethylamino)methyl]benzene |
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Authors: | Johannes G Donkervoort Jos L Vicario Evelien Rijnberg Johann TBH Jastrzebski Huub Kooijman Anthony L Spek Gerard van Koten |
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Institution: | Johannes G. Donkervoort, José L. Vicario, Evelien Rijnberg, Johann T.B.H. Jastrzebski, Huub Kooijman, Anthony L. Spek,Gerard van Koten, |
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Abstract: | The heteroatom assisted lithiation of 1,3-bis1-(dimethylamino)ethyl]benzene with n-BuLi afforded 2,6-bis1-(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-bis1-(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. |
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Keywords: | Heteroatom assisted lithiation Stereoselective crystallization Mixed organolithium aggregate |
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