Generation of 1-azapentadienyl anion from N-(tert-butyldimethylsilyl)-3-buten-1-amine.
N-(tert-Butyldimethylsilyl)-3-buten-1-amine undergoes allylic deprotonation at the 2-position when exposed to 2 equiv of nBuLi in THF. This allylic anion undergoes lithium hydride elimination to generate a 1-azapentadienyl anion. The anion is generated cleanly and completely.
Jacobson
Madeleine A
MA
Department of Chemistry, Brown University, Providence, RI 02912, USA.
Williard
Paul G
PG
D000588:Amines / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D017646:Organosilicon Compounds / Q000737:chemistry*
D000588:Amines; D000838:Anions; D001372:Aza Compounds; C467962:N-(tert-butyldimethylsilyl)-3-buten-1-amine; D017646:Organosilicon Compounds