Reductively activated “Polar” nucleophilic aromatic substitution. II. The reaction of p-dinitrobenzene and p-nitrobenzonitrile with charged and neutral nucleophiles

Mir, Miquel; Espín, Martirio; Marquet, Jacques; Gallardo, Iluminada; Tomasi, Chiara

doi:10.1016/0040-4039(94)88426-9

Cited by 9 publications

(3 citation statements)

References 26 publications

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“…4-Chloro-, 4-bromo-, and 4-iodonitrobenzene all reacted with 4-methoxyphenol to produce the expected diaryl ether in good yields, although long reaction times were needed (entries 33−35, compare to entry 23). While addition of phenol to p -dinitrobenzene provided easy access to 4-phenoxynitrobenzene (entry 36), the addition of 3-methoxyphenol to electronically unfavorable m -dinitrobenzene resulted in no reaction (entry 37). Many different conditions have been used in such nitro displacements for the preparation of diaryl ethers and diarylamines …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6: Expansion of Scope and Utility¹

et al. 1998

J. Org. Chem.

133

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An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the S(N)Ar addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable 3-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6: Expansion of Scope and Utility¹

et al. 1998

J. Org. Chem.

133

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“…A third interpretation of the result of Figure is shown in Scheme . It would take into account the elusive S RN 2 reaction ,− of which no example has ever be found. An attack of the nucleophile on ( E )-4-NO 2 − 1 •- would form an adduct (reaction 20), the cleavage (reaction 21) of which would lead to the radical anion 1-CH(CN) 2 −4-NO 2 − 2 •- and to the final product 2 −1-CH(CN) 2 −4-NO 2 − 2 along reaction 18.…”

Section: Resultsmentioning

confidence: 99%

Isomerization of Azo Compounds. Cleavage Recombination Mechanism of Azosulfides

et al. 1999

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(Z)-4-Nitrophenyl tert-butylsulfide [(Z)-4-NO2−1], upon formation of its radical anion, isomerizes to the (E)-isomer at a very fast rate of 6.3 × 106 s-1, about 103 times faster than azobenzene, while the 4-fluoro tert-butylsulfide (4-F−1) cleaves without isomerization. The particular behavior of 4-NO2−1 is related to the occurrence of a cleavage recombination mechanism, different from the usual inversion rotation mechanism. The existence of a reversible cleavage for the radical anion of 4-NO2−1 bears consequences on the mechanism of SRN1 reactions of azosulfides; the attack of the nucleophile would take place on the intermediate diazenyl radical and not on the ensuing aryl radical as previously proposed.

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“…Some scholars propose a multidimensional concept of integration allowing parallel citizenship while sustaining community ties. 46 Forcing abandonment of modest codes may breed resentment and hinder belonging. 47 A balanced perspective considers individual prioritiessome femmes choose situational unveiling in professional contexts while retaining hijāb spiritually.…”

Section: Cultural Assimilationmentioning

confidence: 99%

Muslim Dress Code and Its Health Benefits

Akanni,

Adam

2023

ojorhv

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This article provided an overview of the history and benefits of Muslim dress code. It traced the origins and evolution of modest clothing styles prescribed in Islam and explored regional variations across Muslim majority cultures. Key benefits of adhering to Islamic dress standards around modesty are examined, including spiritual discipline, health aspects of loose fitting garments, and cultural identity affirmation. Common types of traditional Muslim attire such as hijāb, jalbāb and abāya are defined. The paper also looked at modern trends integrating Islamic dress principles with contemporary fashion design. Issues pertaining to social discussions on Muslim dress code in the context of religious freedom, cultural integration and stereotyping are critically analyzed.

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Reductively activated “Polar” nucleophilic aromatic substitution. II. The reaction of p-dinitrobenzene and p-nitrobenzonitrile with charged and neutral nucleophiles

Cited by 9 publications

References 26 publications

Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6: Expansion of Scope and Utility¹

Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6: Expansion of Scope and Utility¹

Isomerization of Azo Compounds. Cleavage Recombination Mechanism of Azosulfides

Muslim Dress Code and Its Health Benefits

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Reductively activated “Polar” nucleophilic aromatic substitution. II. The reaction of p-dinitrobenzene and p-nitrobenzonitrile with charged and neutral nucleophiles

Cited by 9 publications

References 26 publications

Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6: Expansion of Scope and Utility1

Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6: Expansion of Scope and Utility1

Isomerization of Azo Compounds. Cleavage Recombination Mechanism of Azosulfides

Muslim Dress Code and Its Health Benefits

Contact Info

Product

Resources

About

Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6: Expansion of Scope and Utility¹

Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6: Expansion of Scope and Utility¹