Direct Transfer of the Sulfonylimino Group of Imino-λ<sup>3</sup>-Bromane to <i>N</i>-Heterocycles and Trialkylamines: Synthesis of <i>N</i>-Iminoammonium Ylides under Metal-Free Conditions
Masahito Ochiai
Yufuko Kawano
Takao Kaneaki
Norihiro Tada
Kazunori Miyamoto
10.1021/ol802383f.s001
https://acs.figshare.com/articles/journal_contribution/Direct_Transfer_of_the_Sulfonylimino_Group_of_Imino_sup_3_sup_Bromane_to_i_N_i_Heterocycles_and_Trialkylamines_Synthesis_of_i_N_i_Iminoammonium_Ylides_under_Metal_Free_Conditions/2885425
Exposure of <i>N</i>-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-λ<sup>3</sup>-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-λ<sup>3</sup>-bromane probably serves as an active nitrenoid species without any activation and produces the ammonium ylides via a bimolecular nucleophilic substitution process.
2009-01-15 00:00:00
Imino
Direct Transfer
transfer
variety
sulfonylimino group
nucleophilic substitution process
Ylide
Sulfonylimino Group
ammonium ylides
Exposure
trifluoromethanesulfonylimino
activation
room temperature results
Trialkylamine
iminoammonium ylides
nitrenoid species
nitrogen atoms
Synthesi
aliphatic trialkylamines