Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent

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1-lithio-2-butyl-1,2-dihydropyridines, typically formed as intermediates in the nucleophilic substitution (addition/elimination) of pyridine with (n- or t-) butyl lithium, have been isolated and comprehensively characterized. The linear substituted isomer is polymeric while the branched substituted isomer is a cyclotrimer. The lower oligomerization of the latter complex confers exceptional hexane solubility making it an excellent lithium hydride source in non-polar, aliphatic media.
Original languageEnglish
Pages (from-to)5452-5455
Number of pages4
JournalChemical Communications
Issue number25
Early online date10 Sep 2014
Publication statusPublished - 28 Mar 2015


  • crystallography
  • isomers
  • hexane solubility

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