One-pot regioselective synthesis of nitrophenyloxazolinyl styrene oxides by the Darzens reaction of vicarious nucleophilic substitution-formed carbanions of 2-dichloromethyl-4,4-dimethyloxazoline.

doi:10.1021/JO0498359

Paper

One-pot regioselective synthesis of nitrophenyloxazolinyl styrene oxides by the Darzens reaction of vicarious nucleophilic substitution-formed carbanions of 2-dichloromethyl-4,4-dimethyloxazoline.

Published Jun 18, 2004 · S. Florio, Patrizia Lorusso, C. Granito

The Journal of organic chemistry

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Abstract

The vicarious nucleophilic substitution reaction of dichloromethyloxazoline 2 with nitrobenzene has been investigated. Treatment of 2 with t-BuOK followed by the addition of nitrobenzene leads to benzylic carbanions 4 or 9 depending upon the solvent used (DMSO, DMF, or THF). Subsequent treatment of 4 or 9 with aldehydes, in a Darzens-like reaction, furnishes very good yields of nitrophenyl oxazolinyloxiranes 8 and 11. 1,2-Dioxazolinyl-1,2-dinitrophenylethene 7 forms quantitatively when carbanion 4 is allowed to warm to room temperature in the absence of external electrophiles.

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This study demonstrates a one-pot regioselective synthesis of nitrophenyloxazolinyl styrene oxides using the Darzens reaction of vicarious nucleophilic substitution-formed carbanions of 2-dichloromethyl-4,4-di

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

One-pot regioselective synthesis of nitrophenyloxazolinyl styrene oxides by the Darzens reaction of vicarious nucleophilic substitution-formed carbanions of 2-dichloromethyl-4,4-dimethyloxazoline.

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References

Citations

Introduction of Carbon Substituents into Nitroarenes via Nucleophilic Substitution of Hydrogen: New Developments

Nucleophilic substitution of hydrogen in nitroarenes allows for the introduction of alkyl and functionalized alkyl substituents, leading to the construction of carbo- and heterocyclic rings and the investigation of the mechanism of SNArH.

α-Chlorobenzylation of Nitroarenes via Vicarious Nucleophilic Substitution with Benzylidene Dichloride: Umpolung of the Friedel-Crafts Reaction.

-chlorobenzylated nitrobenzenes can be obtained by combining -dichlorotoluenes with electron-deficient arenes, resulting in six- and five-membered heterocycles.

Efficient synthesis of syn-α-alkoxy epoxide via a diastereoselective Darzens reaction

A diastereoselective Darzens reaction effectively synthesizes syn--alkoxy epoxide using MEM- or TBDPS-protected -hydroxy aldehyde and di-tert-butyl bromomalonate, with a

Nucleophilic Substitution of Hydrogen in Electron‐Deficient Arenes

Nucleophilic substitution of hydrogen is the major primary process in electron-deficient arenes, with conventional SNAr of halogen just secondary ipso substitution.

One-Pot Synthesis of Esters of Cyclopropane Carboxylic Acids via Tandem Vicarious Nucleophilic Substitution-Michael Addition Process.

This one-pot process allows for the synthesis of esters of cyclopropane carboxylic acids with p-nitroaromatic rings, offering a promising strategy for the synthesis of cyclopropane carboxylic acids with p-nitroaromatic rings.

Synthesis of a Camphor-Derived Auxiliary and the Application to the Asymmetric Darzens Reaction

This study presents a highly efficient and short general route for synthesising chiral camphor-derived auxiliary, which can be applied to the asymmetric Darzens reaction for efficient and high yield production of glycidic esters.