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( E/Z ) Equilibria, 16. Lone Electron Pair Donor Quality of the Imino Function: Synthesis and Reactivity of Sterically Strongly Congested Iminocyclopentanes
Author(s) -
Knorr Rudolf,
Hintermeyer;Hilpert Monika,
Mehlstäubl Johann,
Hoang Thi Phung,
Neuner Brigitte,
Bührer Petra
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260129
Subject(s) - chemistry , lone pair , steric effects , nitration , electrophile , protonation , aniline , reactivity (psychology) , nucleophile , medicinal chemistry , double bond , hydrolysis , regioselectivity , stereochemistry , organic chemistry , molecule , medicine , ion , alternative medicine , pathology , catalysis
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 π‐donor quality is assessed by probing weaker electrophiles and by qualitative competition experiments.