A likely intermediate during the CO2-induced activation of 2-alkylindoles toward electrophilic substitution: Structure of a unique tetramer formed by joining two boat-shaped (LiOCO)2 rings

Robert P. Davies, Paul R. Raithby, Ronald Snaith

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Reaction of 2,3-dimethylindole in thf with nBuLi and CO2 gives a lithium carbamate complex (2·thf)n, which has a unique tetrameric solid-state structure (n = 4) containing two boat-shaped (-LiO-COLiOCO-) rings joined by four inter-ring Li-O connections. The two-coordinate O atoms of these rings are near to the 2-Me groups of the indolyl residues, suggesting an explanation for second lithiation (and subsequent electrophilic substitution) of 2-alkylindoles and related heterocyclics occurring specifically at the 2-alkyl position.

Original languageEnglish
Pages (from-to)4355-4356
Number of pages2
Issue number21
Publication statusPublished - 15 Oct 1996

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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