%0 Journal Article
%A Ochiai, Masahito
%A Kawano, Yufuko
%A Kaneaki, Takao
%A Tada, Norihiro
%A Miyamoto, Kazunori
%D 2009
%T Direct Transfer of the Sulfonylimino Group of Imino-λ3-Bromane to N-Heterocycles and Trialkylamines: Synthesis of N-Iminoammonium Ylides under Metal-Free Conditions
%U 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
%R 10.1021/ol802383f.s001
%2 https://ndownloader.figshare.com/files/4583338
%K Imino
%K Direct Transfer
%K transfer
%K variety
%K sulfonylimino group
%K nucleophilic substitution process
%K Ylide
%K Sulfonylimino Group
%K ammonium ylides
%K Exposure
%K trifluoromethanesulfonylimino
%K activation
%K room temperature results
%K Trialkylamine
%K iminoammonium ylides
%K nitrenoid species
%K nitrogen atoms
%K Synthesi
%K aliphatic trialkylamines
%X Exposure of N-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-λ3-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-λ3-bromane probably serves as an active nitrenoid species without any activation and produces the ammonium ylides via a bimolecular nucleophilic substitution process.
%I ACS Publications