3367-61-1Relevant academic research and scientific papers
Deprotonation de N-oxydes d'amines aliphatiques: schema reactionnel general et nouvelle synthese de pyrrolidines
Beugelmans, Rene,Benadjila-Iguertsira, Leila,Chastanet, Jacqueline,Negron, Guillermo,Roussi, Georges
, p. 725 - 734 (2007/10/02)
Amine oxides, 1, 5, 10, 15, 21, 23, when treated by lithium diisopropylamide undergo deprotonation.Monodeprotonation gives rise either to secondary amines and benzaldehyde resulting from the hydrolysis of an intermediate immonium (I) or to hydroxylamines via a Stevens-like rearrangement observed for the first time on an amine oxide.Double deprotonation gives an immonium ylid (Y) which, depending upon the structure of the initial tertiary amine yields either "head to head" piperazines (biradical-like behavior of (DD)) or aziridines.The immonium ylid (Y5) derived from trimethylamine oxide, whose formation and reactivity are reported for the first time, has remarkable property of undergoing cycloaddition reactions with unactivated olefins, leading to a new and efficient synthesis of various pyrrolidines.
