Reactivity in the nucleophilic aromatic substitution reactions of pyridinium ions-Reference-Cited by-同舟云学术

Reactivity in the nucleophilic aromatic substitution reactions of pyridinium ions

Published:2014 Issue:32 Volume:12 Page:6175-6180
ISSN:1477-0520
Container-title:Org. Biomol. Chem.
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Bowler Jeannette T.¹²³,Wong Freeman M.¹²³,Gronert Scott⁴⁵⁶,Keeffe James R.¹²³,Wu Weiming¹²³

Affiliation:

1. Department of Chemistry and Biochemistry

2. San Francisco State University

3. San Francisco, USA

4. Department of Chemistry

5. Virginia Commonwealth University

6. Richmond, USA

Abstract

The nucleophilic aromatic substitution reactions of piperidine with N-methylpyridinium ions in methanol occur via rate determining preassociation of a second piperidine molecule with the addition intermediate followed by barrier-free deprotonation. Loss of leaving group is concurrent with deprotonation for Cl, Br, and I (E2), but subsequent to deprotonation, although rapid, for CN and F (E1cB_IRR).

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2014/OB/C4OB00946K

Reference37 articles.

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4. 113. The organic chemistry of the transition elements. Part I. Tricarbonylchromium derivatives of aromatic compounds

5. 841. Molecular-orbital theory of organometallic compounds. Part IV. Substitution reactions of tricarbonylbenzenechromium

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