5369-36-8Relevant academic research and scientific papers
Amide conformational switching induced by protonation of aromatic substituent
Yamasaki, Ryu,Tanatani, Aya,Azumaya, Isao,Saito, Shoichi,Yamaguchi, Kentaro,Kagechika, Hiroyuki
, p. 1265 - 1267 (2007/10/03)
(Matrix presented) Introduction of an electron-withdrawing group on the aromatic ring of N-methylacetanilide decreased the ratio of the cis conformer, and the ratio correlates well with the Hammett σ values of the substituents. These steric properties can be applied to achieve amide conformational swiching by protonation at the aromatic substituent of 4-[bis(dimethylamino)]-N-methylacetanilide or N-[p-(dimethylamino)phenyl]-N-phenylacetamide.
Addition of NN-Dimethylaniline Oxides to Nitrilium Salts and to Dimethyl Acetylenedicarboxylate. Direct Alkylamination of NN-Dimethylanilines
Sheradsky, Tuvia,Nov, Eliahu
, p. 527 - 530 (2007/10/02)
NN-Dimethylaniline oxide (1) and its ring-substituted derivatives react with N-alkylacetonitrilium salts to give the corresponding 2- and 4-(N-alkylacetamido)dimethylanilines.The mechanism, Which involves migration of an amide group from the aniline nitrogen onto the ring, is discussed.Addition of the oxide (1) to dimethyl acetylenedicarboxylate leads either to demethylation of the aniline (main path in dichloromethane) or to a rearrengement, which involves migration of the succinyl moiety onto the ortho-carbon (in ethanol).
