Concepedia

Nonpolar Solvent a Key for Highly Regioselective S<sub>N</sub>Ar Reaction in the Case of 2,4-Difluoronitrobenzene

Suresh Kumar Sythana, Surendra R. Naramreddy, Santosh Kavitake, Pundlik Rambhau Bhagat

Organic Process Research & Development · 2014 · 13 citations · 13 references

DOI

Concepts

Abstract

A practical and highly regioselective aromatic nucleophilic substitution reaction for the substrate 2,4-difluoronitrobenzene is demonstrated with various O/S/N-nucleophiles. Solvent screens substantiate the role of a nonpolar solvent in ortho -selective nucleophilic substitution through a six-membered polar transition state.

References

13

Organocatalytic Regio- and Asymmetric <i>C</i>-Selective S<sub>N</sub>Ar ReactionsStereoselective Synthesis of Optically Active Spiro-pyrrolidone-3,3‘-oxoindoles

Marco Bella, Sara Kobbelgaard, Karl Anker Jørgensen · Journal of the American Chemical Society · 2005 · 187 citations

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Nitro-Methyl Redox Coupling: Efficient Approach to 2-Hetarylbenzothiazoles from 2-Halonitroarene, Methylhetarene, and Elemental Sulfur

Thanh Bình Nguyễn, Ludmila Ermolenko, Ali Al‐Mourabit · Organic Letters · 2013 · 115 citations

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Continuous Synthesis and Purification by Direct Coupling of a Flow Reactor with Simulated Moving‐Bed Chromatography

Alexander G. O’Brien, Zoltán Horváth, François Lévesque et al. · Angewandte Chemie International Edition · 2012 · 97 citations · Full text

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The ortho: para Ratio in Activation of Aromatic Nucleophilic Substitution by the Nitro Group<sup>1</sup>

J. F. Bunnett, R. J. Morath · Journal of the American Chemical Society · 1955 · 87 citations

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The Kinetics and Mechanisms of Aromatic Nucleophilic Substitution Reactions in Liquid Ammonia

Pengju Ji, John H. Atherton, Michael I. Page · The Journal of Organic Chemistry · 2011 · 57 citations

, , +12