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

Johannes G. Donkervoort, José L. Vicario, Evelien Rijnberg, Johann T B H Jastrzebski, Huub Kooijman, Anthony L. Spek, Gerard Van Koten*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

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 stereo selective 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-C′2-Li2-C framework.

Original languageEnglish
Pages (from-to)463-467
Number of pages5
JournalJournal of Organometallic Chemistry
Volume550
Issue number1-2
Publication statusPublished - 15 Jan 1998

Keywords

  • Heteroatom assisted lithiation
  • Mixed organolithium aggregate
  • Stereoselective crystallization

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