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Experimental Evidence for Intramolecular ipso Substitution of Alkyl Groups
Author(s) -
Zubkov Fedor I.,
Nikitina Eugenia V.,
Kouznetsov Vladimir V.,
Duarte Luz Dary Avellaneda
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400356
Subject(s) - intramolecular force , chemistry , alkylation , alkene , cycloalkane , moiety , alkyl , quinoline , medicinal chemistry , stereochemistry , organic chemistry , catalysis
An acid‐mediated intramolecular Friedel−Crafts intramolecular alkene alkylation of the ortho ‐alkyl group in the N ‐arylamino moiety of various N ‐(1‐allylcycloalkyl)‐ N ‐arylamines resulting in alkyl‐substituted 3′,4′‐dihydro‐1′ H ‐spiro[cycloalkane‐1,2′‐quinolines] is described. The mechanistic details of this intramolecular Friedel−Crafts alkylation by an alkene moiety can be explained by an intramolecular alkylation with ipso substitution of alkyl groups and their 1,2‐rearrangement. The scope and limitations of this reaction were determined. As a conclusive proof of the proposed mechanism, previously unknown interesting by‐products, dispiro[quino[6,7‐ f ]quinoline‐3,1′:9,1′′‐bis(cycloalkanes), were isolated and characterized. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)