A 1,3-sigmatropic rearrangement revealed in the solid and solution state structures of a chiral sodium 1-azaallyl complex derived from (S)-N-(α-methylbenzyl)allylamine

Philip C Andrews, Simone M Calleja, Melissa Maguire, Peter J Nichols

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The reaction of nBuNa with (S)-N-(α-methylbenzyl)allylamine, followed by the addition of tmeda, gives a chiral sodium 1-azaallyl complex, {[(S)-α-[PhC(H)MeN..-C-(H)..-CHCH3)] Na·tmeda}2, as confirmed by single crystal X-ray diffraction and solution NMR spectroscopy, and is most likely the result of a 1,3-sigmatropic rearrangement and subsequent delocalisation within the resulting enamide.

Original languageEnglish
Pages (from-to)1583-1587
Number of pages5
JournalEuropean Journal of Inorganic Chemistry
Publication statusPublished - 1 Jan 2002


  • Amines
  • Chirality
  • N ligands
  • Sigmatropic rearrangement
  • Sodium
  • Structure elucidation

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