A nitro-hunsdiecker reaction: from unsaturated carboxylic acids to nitrostyrenes and nitroarenes.

doi:10.1021/OL0262901

Paper

A nitro-hunsdiecker reaction: from unsaturated carboxylic acids to nitrostyrenes and nitroarenes.

Published Aug 3, 2002 · J. Das, P. Sinha, Sujit Roy

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Abstract

[reaction: see text] The nitrodecarboxylation of aromatic alpha,beta-unsaturated carboxylic acids and ring-activated benzoic acids can be achieved using nitric acid (3 equiv) and catalytic AIBN (2 mol %) in MeCN. From the effect of various additives, the nitrodecarboxylation is postulated to involve the generation of an acyloxy radical RCO(2)(*) by a NO(3)(*) radical followed by attack of a NO(2)(*) radical.

Study Snapshot

This nitrodecarboxylation of aromatic unsaturated carboxylic acids and ring-activated benzoic acids can be achieved using nitric acid (3 equiv) and catalytic AIBN (2 mol %) in MeCN, with the reaction involving the generation of an acyloxy

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

A nitro-hunsdiecker reaction: from unsaturated carboxylic acids to nitrostyrenes and nitroarenes.

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References

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Nitration of uracil base and nucleoside derivatives with nitric acid can efficiently produce biologically active compounds with potential therapeutic applications.

Side-Chain Nitration of Styrene and Para-Substituted Derivatives with a Combination of Nitrogen Dioxide and Ozone

This study demonstrates the potential of kyodai nitration for the synthesis of styrene and para-substituted derivatives, with excellent yields and a smooth addition reaction across the olefinic bond in dichloromethane at 20°C.

Electrophilic aromatic substitution. Part 37. Products of aromatic nitrations of some chloronitrobenzenes and substituted benzoic acids in solutions of dinitrogen pentaoxide and of nitronium salts in nitric acid

A novel mechanism for aromatic nitration of chloronitrobenzenes and substituted benzoic acids in nitric acid solutions involves reversible addition of the NO3 radical followed by combination with NO2, leading to aromatic nitroproducts.

Electrophilic aromatic substitution. Part 36. Kinetics of aromatic nitrations in solutions of dinitrogen pentaoxide and of nitronium salts in nitric acid

Dinitrogen pentaoxide solutions show similar nitration rates to nitronium salt solutions, with some exceptions, and rate enhancements at high concentrations are largely medium effects.

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,-unsaturated -nitrocarboxylic esters can be synthesized by treating,-unsaturated carboxylic ester with fuming nitric acid, resulting in -methoxy--nitrocarboxylic ester and

Citations

Catalytic chemo and homoselective ipso-nitration under mild condition

This study presents a new selective nitration methodology using MOFs/sodium nitrite for chemo and homoselective ipso-nitration of a wide range of compounds under mild conditions without using acid nitric.

From N–H Nitration to Controllable Aromatic Mononitration and Dinitration—The Discovery of a Versatile and Powerful N-Nitropyrazole Nitrating Reagent

The N-Nitropyrazole nitrating reagent enables mild and scalable nitration of a broad range of (hetero)arenes, offering potential for medicinal chemistry and agrochemicals.

Recent developments in decarboxylative C(aryl)-X bond formation from (hetero)aryl carboxylic acids.

Decarboxylative coupling reactions using (hetero)aryl carboxylic acids are an efficient and environmentally friendly method for forming new C-C and C-X bonds, with potential for future research opportunities.

Recent progress in the nitration of arenes and alkenes.

Recent progress in regiospecific nitration of aromatics and olefins has achieved excellent functional group tolerance and site-selectivity, enabling the preparation of nitrogen-containing compounds in the chemical industry.

Recent advances in nitro-involved radical reactions

Recent advances in nitro-involved radical reactions have significantly improved access to nitro-containing compounds, enabling efficient and rapid transformations.