Does Activation of the Anti Proton, Rather than Concertedness, Determine the Stereochemistry of Base-Catalyzed 1,2-Elimination Reactions? Anti Stereospecificity in E1cB Eliminations of β-3-Trifluoromethylphenoxy Esters, Thioesters, and Ketones-Reference-Cited by-同舟云学术

Does Activation of the Anti Proton, Rather than Concertedness, Determine the Stereochemistry of Base-Catalyzed 1,2-Elimination Reactions? Anti Stereospecificity in E1cB Eliminations of β-3-Trifluoromethylphenoxy Esters, Thioesters, and Ketones

Published:2012-02-24 Issue:6 Volume:77 Page:2819-2828
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Mohrig Jerry R.¹,Beyer Brandon G.¹,Fleischhacker Angela S.¹,Ruthenburg Alex J.¹,John Seth G.¹,Snyder Daniel A.¹,Nyffeler Paul T.¹,Noll Robert J.¹,Penner Nicholas D.¹,Phillips Laura A.¹,Hurley Heidi L. S.¹,Jacobs Jon S.¹,Treitel Corinna¹,James Thomas L.¹,Montgomery Martha P.¹

Affiliation:

1. Department of Chemistry, Carleton College, Northfield, Minnesota 55057, United States

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo300053w

Reference53 articles.

1. Distinguishing between concerted and nonconcerted eliminations

2. Novel Syn Intramolecular Pathway in Base-Catalyzed 1,2-Elimination Reactions of β-Acetoxy Esters

3. Stereochemistry of 1,2-elimination reactions at the E2–E1cB interface—tert-butyl 3-tosyloxybutanoate and its thioester

4. Free-Energy Surfaces for Liquid-Phase Reactions and Their Use To Study the Border Between Concerted and Nonconcerted α,β-Elimination Reactions of Esters and Thioesters

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