Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites

Smith, Keith; El‐Hiti, Gamal A.; Hammond, Mark E. W.; Bahzad, Dawoud; Li, Zhaoqiang; Siquet, Christophe

doi:10.1039/b002157l

Cited by 68 publications

(57 citation statements)

References 13 publications

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“…They injected their own samples and acquired the data on the GC−MS instrument. Initially, methylene chloride was used as the solvent, as suggested in the original literature procedure, 6 but later this was changed to the greener choice of cyclohexane with very comparable results.…”

Section: ■ Experimentsmentioning

confidence: 99%

“…The product mixture can be analyzed by GC. 6 Alternatively, 1 H NMR spectroscopy can be used to study the reaction mixture, or the experiment can be pursued as a traditional synthesis if desired (details for the latter two options are discussed in greater detail in the Supporting Information). GC−MS was used here because it was pedagogically convenient to cover certain aspects of mass spectrometry.…”

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confidence: 99%

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Introduction of a Simple Experiment for the Undergraduate Organic Chemistry Laboratory Demonstrating the Lewis Acid and Shape-Selective Properties of Zeolite Na-Y

2017

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A simple, inexpensive, discovery-based experiment for undergraduate organic laboratories has been developed that demonstrates the Lewis acid and shape-selective properties of zeolites. Calcined zeolite Na-Y promotes the electrophilic aromatic bromination of toluene with a significantly higher para/ortho ratio than observed under conventional conditions. The experiment can be completed in one three-hour laboratory period. The zeolite can be recovered and regenerated for later reuse. A broad range of organic course topics from orientation in electrophilic aromatic substitution to photochemistry can be discussed.

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Section: ■ Experimentsmentioning

confidence: 99%

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confidence: 99%

Introduction of a Simple Experiment for the Undergraduate Organic Chemistry Laboratory Demonstrating the Lewis Acid and Shape-Selective Properties of Zeolite Na-Y

2017

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“…12 We have shown that zeolites and other solid catalysts can play an important role in the enhancement of regionselectivity in nitration processes [13][14][15][16][17][18][19][20][21][22] and in many other electrophilic aromatic substitution reactions. [23][24][25][26][27][28][29][30][31] For example, 2,4-DNT was successfully produced in 96% yield with a 2,4-:2,6-DNT ratio of 70:1 by simple direct dinitration of toluene over a HNO 3 /acetic anhydride (Ac 2 O)/trifluoroacetic anhydride (TFAA)/Hβ system in two steps.…”

Section: Introductionmentioning

confidence: 99%

Regioselective nitration of 2- and 4-nitrotoluenes over systems comprising nitric acid, an acid anhydride and a zeolite

Smith¹,

Alotaibi²,

El‐Hiti³

et al. 2014

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Abstract:Nitration of 2-nitrotoluene using nitric acid, acetic anhydride and Hβ zeolite produces a 97% yield of 2,4-dinitotoluene along with 3% of 2,6-dinitrotoluene. Nitration of 4-nitrotoluene under similar reaction conditions produces 2,4-dinitrotoluene in 89% yield. When chloroacetic anhydride was used instead of acetic anhydride, nitration of 4-nitotoluene produced a quantitative yield (99%) of 2,4-nitrotoluene.

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“…[5][6][7][8][9][10][11] We have reported the successful use of zeolites in various electrophilic aromatic substitution reactions. [12][13][14] We have shown that the zeolites can be used in greener para-regioselective reactions including nitration, [15][16][17][18][19][20][21] alkylation, 22,23 acylation, 24,25 halogenation 26,27 and methanesulfonylation 28 reactions.…”

Section: Introductionmentioning

confidence: 99%

Regioselective dinitration of simple aromatics over zeolite Hβ/nitric acid/acid anhydride systems

Smith¹,

Alotaibi²,

El‐Hiti³

2014

Arkivoc

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Various nitration systems comprising nitric acid, acid anhydride and zeolite Hβ in the absence of solvent are described. Direct double nitration of toluene with a nitric acid, propanoic anhydride and zeolite H system has been developed to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of 123:1. This system also nitrates activated mono-substituted benzenes (anisole and phenetole) and moderately activated mono-substituted benzenes (ethylbenzene and propylbenzene) to give mainly 2,4-dinitro derivatives. The zeolite can be recovered, regenerated and reused to give almost the same yield as that given when fresh zeolite is used.

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Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites

Cited by 68 publications

References 13 publications

Introduction of a Simple Experiment for the Undergraduate Organic Chemistry Laboratory Demonstrating the Lewis Acid and Shape-Selective Properties of Zeolite Na-Y

Introduction of a Simple Experiment for the Undergraduate Organic Chemistry Laboratory Demonstrating the Lewis Acid and Shape-Selective Properties of Zeolite Na-Y

Regioselective nitration of 2- and 4-nitrotoluenes over systems comprising nitric acid, an acid anhydride and a zeolite

Regioselective dinitration of simple aromatics over zeolite Hβ/nitric acid/acid anhydride systems

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