Knorr, R. and Thi, Phung Hoang and Mehlstäubl, J. and Hintermeyer-Hilpert, M. and Lüdemann, H.-D. and Lang, Elmar and Sextl, G. and Rattay, W. and Böhrer, P.
Lone-electron pair donor quality of the imino function: Increased front strain and electronic substituent effects on sterically accelerated nitrogen inversion in imino-cyclopentanes.
Chemische Berichte 126 (1), pp. 217-224.
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Other URL: http://onlinelibrary.wiley.com/doi/10.1002/cber.19931260129/pdf
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.
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