Synthesis and Crystallographic Characterization of X-Substituted 2,4-Dinitrophenyl-4′-phenylbenzenesulfonates

Stenfors, Brock A.; Staples, Richard J.; Biros, Shannon M.; Ngassa, Felix N.

doi:10.3390/chemistry2020036

Cited by 7 publications

(4 citation statements)

References 16 publications

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“…Reactions involving pyridine were conducted under an inert atmosphere due to concerns regarding the hydrolysis of the N-tosylpyridinium salt intermediate. Previously reported work provides mechanistic insight into the formation of Ntosylpyridinium in the context of sulfonates [28]. However, after achieving higher yields in the presence of aqueous pyridine and tetrahydrofuran it was concluded that the rate of hydrolysis is insignificant compared to the solvent and base combination chosen.…”

Section: Tosylation Of Aminesmentioning

confidence: 95%

The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives

Stenfors

Ngassa

2021

Eur. J. Chem.

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The sulfonamide moiety is present among a variety of biologically significant compounds. A facile synthesis is necessary to produce a variety of sulfonamides with the potential to improve human health. Herein, we report a facile methodology for the synthesis of 4-methylbenzenesulfonamides, amenable to a broad range of nitrogen nucleophiles. Implementing a semi-miscible biphasic solvent system resulted in higher yields, decreased reaction times, and a simplified workup over preliminary methods. Additionally, the crystal structures of five novel sulfonamide compounds and two polymorphs, have been determined by X-ray diffraction. Results obtained through spectroscopic characterization support the successful formation of the desired 4-methylbenzenesulfonamides.

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Section: Tosylation Of Aminesmentioning

confidence: 95%

The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives

Stenfors

Ngassa

2021

Eur. J. Chem.

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“…The synthetic strategy employed in this work has been previously reported by our group [30]. Initial reaction conditions of dichloromethane in the presence of pyridine resulted in the formation of an undesired pyridinium salt as the only product.…”

Section: Synthetic Techniquesmentioning

confidence: 99%

Crystal structure of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate

Stenfors

Ngassa

2022

Eur J Chem

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Arylsulfonates are a useful class of synthetic precursors, affording either their arylamine or arylsulfonamide counterparts upon amination via regioselective C–O/S–O bond cleavage. Herein, the synthesis of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate is described, utilizing our previously developed synthetic methods, and crystallographic characterization. While the mechanism for nucleophilic substitution at the sulfonyl group remains largely unknown, experimental work within our group and in the literature lend credence to a mechanism analogous to its carbonyl counterpart. Characterization of the molecular structure of the title compound, C15H14N2O7S, at 173 K, features a sulfonate group with S=O bond lengths of 1.4198(19) and 1.4183(19) Å and a S–O bond length of 1.6387(18) Å. Viewing down the S–O bond reveals gauche oriented aromatic rings. Crystal data for C15H14N2O7S: Monoclinic, space group P21/c (no. 14), a = 6.8773(10) Å, b = 8.9070(14) Å, c = 25.557(4) Å, β = 93.0630(18)°, V = 1563.3(4) Å3, Z = 4, T = 173.15 K, μ(MoKα) = 0.251 mm-1, Dcalc = 1.557 g/cm3, 12259 reflections measured (3.192° ≤ 2Θ ≤ 50.682°), 2861 unique (Rint = 0.0493, Rsigma = 0.0419) which were used in all calculations. The final R1 was 0.0457 (I > 2σ(I)) and wR2 was 0.1306 (all data).

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“…19 2,4-Dinitrophenyl 4-toluenesulfonate was synthesized according to the literature. 31 (CAUTION: 2,4-Dinitrophenol under certain situations can be explosive 32 and should be handled with care). 2,4-Dinitrophenol moistened with 15% of water, (150.1 mg, 0.69 mmol) was dissolved in distilled THF (1.4 mL).…”

Section: -Nitrophenyl 4-toluenesulfonate (Ts-4-np 2e)mentioning

confidence: 99%

Comparison of Various Tosylating Reagents for the Synthesis of Mono-2-O-tosyl-β-cyclodextrin

Kordopati¹,

Konstantinou²,

Tsivgoulis³

2022

Synthesis

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Mono-2-O-tosyl-β-cyclodextrin is a key compound, as starting material, for the preparation of multifunctional systems in supramolecular chemistry. Although several methods are available in the literature for its synthesis, yields are always moderate (usually less than 42%) and reproducibility can be an issue as a result of the difficulties encountered in its preparation that are related to selectivity, monofunctionalization, solubility and purification, among others. A modification of a literature method was developed giving emphasis to simplicity and reproducibility and, for the first time, was tested with nine easily accessible tosylating reagents that differ significantly in their nature and reactivity. Product isolation was accomplished with precipitation followed by reverse-phase flash chromatography, which is easy to scale up. Interestingly, with the proposed method, all nine reagents can be successfully applied for the synthesis of the product with yields ranging from 33% to 40%. Optimum reaction times and temperatures were found and conclusions for each tosylating reagent are drawn.

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Synthesis and Crystallographic Characterization of X-Substituted 2,4-Dinitrophenyl-4′-phenylbenzenesulfonates

Cited by 7 publications

References 16 publications

The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives

The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives

Crystal structure of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate

Comparison of Various Tosylating Reagents for the Synthesis of Mono-2-O-tosyl-β-cyclodextrin

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