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Lone-electron pair donor quality of the imino function: Increased front strain and electronic substituent effects on sterically accelerated nitrogen inversion in imino-cyclopentanes

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. (1993) 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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Abstract

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 ...

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Item Type:Article
Date:1993
Institutions:Biology, Preclinical Medicine > Institut für Biophysik und physikalische Biochemie > Prof. Dr. Elmar Lang
Identification Number:
ValueType
10.1002/cber.19931260130DOI
Keywords:Imines; Steric acceleration; Substituent constants; Substituent effects
Subjects:500 Science > 570 Life sciences
Status:Published
Refereed:Unknown
Created at the University of Regensburg:Unknown
Owner: Universitätsbibliothek Regensburg
Deposited On:20 Oct 2010 05:51
Last Modified:13 Mar 2014 19:25
Item ID:17392
Owner Only: item control page

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