The title compound, C13H10N2O7S, was synthesized via a nucleophilic substitution reaction between 2,4-di-nitro-phenol and p-toluene-sulfonyl chloride. This crystal structure is a polymorph of CSD entry WUVYUH [Vembu et al. (2003). Acta Cryst, E59, o378-380]. The aromatic substituents on the sulfonate group are oriented gauche to one another with a C-O-S-C torsion angle of -62.0 (3)°. The supra-...

New unsymmetrical trans-stilbenes have been prepared by the sequential coupling reactions of bromobenzenesulfonate with formylarylboronic acids, benzylphosphonates and arylmagnesium bromides and characterized. The nickel-catalyzed reactions of stilbenesulfonates with aryl Grignard reagents produced the corresponding stilbenes via the nucleophilic aromatic substitution of the neopentyloxysulfony...

Intramolecular nucleophilic aromatic substitution (Truce–Smiles rearrangement) of the anions 2-benzyl benzanilides leads to triarylmethanes in an operationally simple manner. The reaction succeeds even without electronic activation ring that plays role electrophile SNAr reaction, being accelerated instead by preferred conformation imposed tertiary amide tether. substituent product may be remove...

A multistep synthesis of quinolone antibiotic analogues was developed as a laboratory experiment for intermediate/advanced undergraduate students. Students can synthesize range desfluoroenoxacin via five-step sequence. The includes key practical techniques including thin-layer chromatography (TLC), liquid–liquid extraction, trituration, recrystallization, and the characterization compounds by I...

The generation of common and stereochemically rich medium-sized benzo-fused sultams via complementary pairing of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohols/amines in a modular one-pot, sequential protocol using an aziridine ring opening and intramolecular nucleophilic aromatic substitution is reported. The strategy employs a variety of am...

The use of domino and multicomponent reactions in asymmetric synthesis is constantly increasing nowadays. This allows for the synthesis of complex molecules in a single synthetic sequence, usually with high atom economy. Herein, we report three examples of new asymmetric tandem reactions recently developed in our laboratories, giving rise to new families of enantiomerically enriched fluorinated...

Continuous-flow multistep synthesis is combined with quasi-continuous final-product purification to produce pure products from crude reaction mixtures. In the nucleophilic aromatic substitution of 2,4-difluoronitrobenzene with morpholine followed by a heterogeneous catalytic hydrogenation, the desired monosubstituted product can be continuously separated from the co- and by-products in a purity...

A method has been developed for the synthesis of semicrystalline poly(arylene ether ether sulfide) materials by first preparing a soluble, amorphous sulfoxide containing precursor, then rapidly reducing the sulfoxide moiety to sulfide. The sulfoxide polymers are synthesized using conventional nucleophilic aromatic substitution reactions between difluorodiphenyl sulfoxide and diphenols. Reductio...

A novel, efficient, time-saving and reliable radiolabeling procedure via nucleophilic substitution with [(18)F]fluoride is described. Different radiolabeled aliphatic and aromatic compounds were prepared in high radiochemical yields simply by heating of quaternary anilinium, diaryliodonium and triarylsulfonium [(18)F]fluorides in suitable solvents. The latter were obtained via direct elution of...