Why Do Enolate Anions Favor O-Alkylation over C-Alkylation in the Gas Phase? The Roles of Resonance and Inductive Effects in the Gas-Phase SN2 Reaction between the Acetaldehyde Enolate Anion and Methyl Fluoride-Reference-Cited by-同舟云学术

Why Do Enolate Anions Favor O-Alkylation over C-Alkylation in the Gas Phase? The Roles of Resonance and Inductive Effects in the Gas-Phase SN2 Reaction between the Acetaldehyde Enolate Anion and Methyl Fluoride

Published:2016-04-12 Issue:9 Volume:81 Page:3711-3719
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Seitz Christian G.¹,Zhang Huaiyu²,Mo Yirong²,Karty Joel M.¹

Affiliation:

1. Department of Chemistry, Elon University, Elon, North Carolina 27244, United States

2. Department of Chemistry, Western Michigan University, Kalamazoo, Michigan 49008, United States

Funder

Division of Chemistry

Elon University

China Scholarship Council

Division of Computer and Network Systems

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.joc.6b00351

Reference56 articles.

1. Smith, M. B.; March, J.InAdvanced Organic Chemistry: Reactions, Mechanisms and Structure;5th ed.John Wiley & Sons, Inc.:New York, 2001; p551.

2. Nonlocal (Pair Site) Reactivity from Second-Order Static Density Response Function: Gas- and Solution-Phase Reactivity of the Acetaldehyde Enolate as a Test Case

3. Alkylation of enolate ions

4. Origin of Regioselectivity in the Reactions of Nitronate and Enolate Ambident Anions

5. Transition structures for C- and O-alkylation of acetaldehyde enolate. Stereoelectronic effects and carbon/oxygen alkylation ratios

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