Direct transfer of the sulfonylimino group of imino-lambda3-bromane to N-heterocycles and trialkylamines: synthesis of N-iminoammonium ylides under metal-free conditions.
Exposure of N-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-lambda(3)-bromane at room temperature results in direct transfer of the sulfonylimino group to the nitrogen atoms and affords a variety of iminoammonium ylides under transition-metal-free conditions. The imino-lambda(3)-bromane probably serves as an active nitrenoid species without any activation and produces the ammonium ylides via a bimolecular nucleophilic substitution process.
Ochiai
Masahito
M
Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph.tokushima-u.ac.jp
Kawano
Yufuko
Y
Kaneaki
Takao
T
Tada
Norihiro
N
Miyamoto
Kazunori
K
D000588:Amines / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007700:Kinetics; D008670:Metals / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis*; D013696:Temperature
D000588:Amines; D006571:Heterocyclic Compounds; D006842:Hydrocarbons, Brominated; D007097:Imines; D008670:Metals; D000644:Quaternary Ammonium Compounds; D009584:Nitrogen