Aromatic Sulfonyl Chlorides Research Articles

ChemInform Abstract: Studies on 2,5‐Disubstituted 1,3,4‐Oxadiazoles. Part 2. Preparation and Antimicrobial Activity of 2‐Arylsulfonamido/α‐Carbamylarylmethylamino‐5‐(4′‐pyridyl)‐1,3,4‐oxadiazo# les.

AbstractIsoniazide (I) is treated with cyanogen bromide (II) to give the 2‐amino‐1,3,4‐oxadiazole (III) which reacts with the aromatic sulfonyl chlorides (IV), yielding the sulfonamides (V).

Reactions of sodium borohydride. IV. Reduction of aromatic sulfonyl chlorides with sodium borohydride.

Aromatic sulfonyl chlorides were reduced with sodium borohydride in tetrahydrofuran at 0 C to the corresponding sulfinic acids in good yields. Further reduction proceeded when the reaction was carried out under reflux in tetrahydrofuran to give disulfide and thiophenol derivatives via sulfinic acid. Furthermore, sulfonamides were reduced with sodium borohydride by heating directly to give sulfide, disulfide and thiophenol derivatives, and diphenyl sulfone was reduced under similar conditions to give thiophenol and biphenyl

Hetarylation of 1-methylpyrrole by isoquinoline in the presence of aromatic or aliphatic sulfonyl chlorides

When N-alkyl(or aryl) sulfonylisoquinolinium salts are reacted in situ with 1-methylpyrrole, 2-aryl (or alkyl) sulfonyl-1-(pyrrole-2-yl)-1,2-dihydroixoquinolines and 2,5-di[2-aryl(or alkyl)-sulfonyl-1,2-dihydroisoquinolin-1-yl]-1-methylpyrroles form with high yields.

Reactions of metal tert-butoxides with aromatic sulfonyl chlorides. A new synthesis of di-tert-butyl ether

Reactions of metal tert-butoxides with aromatic sulfonyl chlorides. A new synthesis of di-tert-butyl ether

Reactions of metal tert-butoxides with aromatic sulfonyl chlorides. A new synthesis of di- tert-butyl ether

Di- tert-butyl ether was synthesized in good yields by the S N reactions of lithium tert-butoxide with tosyl and p-bromobenzenesulfonyl chlorides under mild conditions.

A Novel Reaction of Aromatic Sulfonyl Chlorides and Thiols

Abstract According to the literature, the reaction of aromatic sulfonyl chlorides with aromatic thiols gives equimolar amounts of disulfide and sulfinic acid.1−3 The reaction sequence is:4 Under certainconditions the reaction can be partially arresedat the first stage, and thiosulfonate can be isolated in yields up to 25 %.5 The possibility of synt he sizing disulfidesexclusively from thiols and sulfonyl chlorides has receivedlittle attention, with the exception of a few cases in which cyclicdisulfides were prepared.6,7

２‐アミノフェナレンと芳香族スルホニルクロリド，芳香族および脂肪族ジカルボニルクロリドから得られるスルホニルアミノフェナレノン類およびアシルアミノフェナレノン類

Sulfonylaminophenalenones and acylaminophenalenones were synthesized by the acylation of 2-amino phenalenone with aromatic sulfonyl chlorides and aromatic or aliphatic dicarboxylic chlorides. The visible absorption spectra of these compounds were measured. The wave number (ν) corresponding to the absorption maxima λmax of 2- (p-substituted phenylsulfonyl) amino-1-phenalenones were linearly related to the Hammett's substituent constants (σ) (ρ+0.038). Their dyeing properties as disperse dye on polyester fiber were examined. Dyeabilities of the 2-sulfonylamino-1-phenalenones were good, but those of the acylaminophenalenones were poor. The colors of dyed cloth were yellow except for the 2, 2'-phthaloylaminodi (1-phenalenone) (pale reddish yellow). Most of the dyed fiber showed good fastness to light and to sublimation, especially sublimation fastness of the acylaminophenalenones were excellent.

Reaction of trialkylborane. IV. Reaction of trialkylborane with aromatic sulfonyl chlorides (author's transl)

Reaction of trialkylborane (I or II) with aromatic sulfonyl chloride derivatives (III-VIII) caused reductive alkylation and afforded the corresponding alkyl aryl sulfides (IX-XX) with a small quantity of mercaptans and disulfides. In this reaction, the yield of alkyl aryl sulfide was considerably better than that in the reaction with diphenyl sulfide (XXII) or sulfenyl chloride (XXIII) under the same condition. In the case of cyclohexyl phenyl sulfone (XXIV), a small amount of alkyl aryl sulfide was obtained, and diphenyl sulfone (XXV) did not react with trialkylborane. Since the reaction of trialkylborane with aromatic sulfonyl chloride was inhibited in the presence of a radical scavenger such as iodine or galvinoxyl, this reaction was considered to include a radical reaction.

Dipole moments, anisotropies of the polarizability, and conformations of aliphatic and aromatic sulfonyl chlorides

1. The ellipsoids of polarizability of dimethylsulfone, sulfuryl chloride, and methanesulfonyl chloride were determined, and the nonadditivity of the parameters of the bonds in the sulfonyl chloride group was demonstrated. 2. Substituted methane sulfonyl chloride exist in gauche conformations. 3. In benzenesulfonyl chloride and a series of its para-substituted derivatives, the aryls are situated in the C-S-Cl plane; the para-nitro group induces a 35° rotation.

Reaction of thionaphthene 1,1-dioxides with aromatic sulfonyl and sulfenyl chlorides

Reaction of thionaphthene 1,1-dioxides with aromatic sulfonyl and sulfenyl chlorides

Polyarylsulfones, synthesis and properties,

AbstractA new class of high molecular weight polyarylsulfones is described. Polymer synthesis and structure–property relationships are discussed. The polymers are prepared by Friedel‐Crafts type polycondensation of aromatic sulfonyl chlorides with aromatic hydrocarbons. A number of Lewis acids in small quantities are useful as catalysts for the polymerization. The polymerization reaction is carried out at elevated temperatures in the melt or in solution. Inert, nonbasic solvents which are compatible with the Lewis acid catalysts such as nitrobenzene and dimethyl sulfone are useful for conducting the polymerization. Many of the polyarylsulfones are amorphous, rigid thermoplastics with unusually high softening points, having glass transition temperatures in the range of 200–350°C. Outstanding resistance to air oxidation at high temperatures is derived from incorporation of the deactivating sulfone groups in the aromatic polymer backbone. Melt stability and solubility in selected solvents are emphasized as basis for processibility by conventional solution casting and molding techniques. The combination of properties, which in addition to thermal stability includes a high level of mechanical and electrical properties, chemical inertness, and hydrolysis resistance makes these new arylsulfone polymers useful over a wide temperature range and in severe and corrosive environments.

Spektroskopische untersuchungen organischer schwefelverbindungen—VII über eine vorbande zur antisymmetrischen SO 2-valenzschwingung in den infrarotspektren substituierter aromatischer sulfochloride

The experimental behaviour of a weak absorption band accompanying the antisymmetrical SO 2 stretching vibration in the infra-red spectra of aromatic sulfonyl chlorides has been investigated. In agreement with the results obtained for different substituents, different concentrations and deuteration this band is interpreted as a “hot band”. The dependence on temperature has been proved.

Spektroskopische untersuchungen organischer schwefelverbindungen—VI. Fermi-resonanz und substituentenverhalten der symmetrischen SO 2-valenzschwingung in den IR-spektren aromatischer sulfochloride

Fermi resonance between the first overtone of the symmetrical SO 2 bending vibration and the symmetrical SO 2 stretching vibration in the spectra of aromatic sulfonyl chlorides has been proved by varying substituents and solvents. The vibrational assignment is given for the region near 1200 cm −1. Changing the SO double bond character by variation of concentration, solvents, and substituents the wavenumber of the symmetrical SO 2 stretching vibration is lowered less than the antisymmetrical one. A linear relationship was found between the wavenumber of the symmetrical SO 2 stretching vibration of ortho substituted aromatic sulfonyl chlorides and Taft's σ constants.

Les α-chloro-énamines—I : Acylation des Ynamines

Acid chlorides, phosgene, thiophosgene, thionyl chloride and aromatic sulfonyl chlorides readily add to ynamines to give α-chloro-enamines. The α-chloro-β-chlorocarbonyl-enamines (V) are thermally remarkably stable as illustrated by their distillation in vacuum without decomposition. The reaction of ynamines with oxalyl chloride led to 5-disubsituted amino-2,2-dichloro-3 (2H)-furanones (XIX) The structure of these α-chloro-enamines was established by hydrolysis, alcoholysis and aminolysis.

Spektroskopische untersuchungen organischer schwefelver-bindungen—V. Studium des substituenteneinflusses an aromatischen sulfochloriden

Zusammenfassung The influence of different substituents in ortho, meta and para position on the wave-numbers of the two SO2 deformation vibrations, and on the wavenumber and the absolute integrated intensity of the antisymmetrical SO2 stretching vibration is investigated for substituted aromatic sulfonyl chlorides. A nearly linear relationship is found between the wavenumber of the antisymmetrical SO2 stretching vibrations and the σ-values given by H ammett and T aft . The relation between concentration and substitution effects is discussed.

Desulfonylation of aromatic sulfonyl chlorides. A new synthesis of aryl chlorides

Desulfonylation of aromatic sulfonyl chlorides. A new synthesis of aryl chlorides

Molecular and crystal structure of ferrocenedisulfonyl chloride

1. The structure of ferrocendisulfonyl chloride was investigated. The interatomic distances and valence angles were found. The shortest intermolecular distances were calculated. 2. On the basis of the data obtained, it was shown that there is an intimate electronic interaction between the ferrocene nucleus and the sulfonyl chloride group, which leads to a redistribution of bond lengths and a decrease in the chemical activity of the chlorine in the sulfonyl chloride group in comparison with normal aromatic sulfonyl chlorides.

Reactions of Aromatic Sulfonyl Chlorides with Organocadmium Reagents*,1

Reactions of Aromatic Sulfonyl Chlorides with Organocadmium Reagents^*,1