Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

8-1983

Journal or Book Title

The Journal of Organic Chemistry

Volume

48

Issue

17

First Page

2936

Last Page

2937

DOI

10.1021/jo00165a034

Abstract

Intermolecular amidoalkylation reactions on aromatic rings constitute an effective strategy for the construction of heterocyclic c0mpounds.l A variety of substituents, including nitro groups, can be accommodated on the aromatic ring. However, anilines or acetanilides react with acyl iminium ions to afford mixtures of products in only modest yields.2 Moreover, the reactions with both o- and p-toluidine yield products wherein the position of substitution of the electrophile is directed by the methyl groupq3 This reactivity profile is due to deactivation by the iminium salt that is produced either by protonation in an acid-catalyzed reaction or by complexation with the Lewis acid catalyst.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 48(17); 2936-2937. Doi: 10.1021/jo00165a034. Copyright 1983 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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