142294-72-2Relevant academic research and scientific papers
(E/Z) Equilibria, 16. Lone Electron Pair Donor Quality of the Imino Function: Synthesis and Reactivity of Sterically Strongly Congested Iminocyclopentanes
Knorr, Rudolf,Hintermeyer-Hilpert, Monika,Mehlstaeubl, Johann,Hoang, Thi Phung,Neuner, Brigitte,Boehrer, Petra
, p. 211 - 216 (2007/10/02)
2,6-Dimethyl-N-(2,2,5,5-tetramethylcyclopentylidene)aniline (4h) is obtained by permethylation; it forms salts (5) by N-protonation.Its CN double bond is strongly shielded against nucleophilic attack and cannot be hydrolyzed.Nitration and bromination occur smoothly in the aromatic p-position (12, 13), showing the directing power of the lone electron pair of the imino function.This ?-donor quality is assessed by probing weaker electrophiles and by qualitative competition experiments. Key Words: Imines / Permethylation / Substitution, electrophilic aromatic / Steric shielding
