Benzenesulfonyl chloride reagent

Heating the oxime with 85% sulfuric acid to prepare 2-piperidone caused eruption of the stirred flask contents. Benzenesulfonyl chloride in alkali is a less vigorous reagent [1], A similar reaction using 70% acid and methanol solvent proceeded uneventfully until vacuum distillation to remove volatiles had been completed at 90° C (bath)/27 mbar when the dark residue exploded [2],... 

From the beginning of the 1960s, the progress in depsipeptide chemistry was connected with the utilization and further development of the mixed anhydride approach for the initial formation of the ester link between a suitably N-protected amino acid and the hydroxy acid ester. The reagent predominantly applied for the construction of the depsipeptide unit was benzenesulfonyl chloride in pyridine. This reagent, introduced by Shemyakin and co-workers in depsipeptide chemistry, was shown to be an efficient reagent for the formation of the ester bond between a protected amino acid and the hydroxy add component (Scheme 4).[21 22 ... 

In absence of diluent or other effective control of reaction rate, the sulfoxide reacts violently or explosively with the following acetyl chloride, benzenesulfonyl chloride, cyanuric chloride, phosphorus trichloride, phosphoryl chloride, tetrachlorosilane, sulfur dichloride, disulfur dichloride, sulfuryl chloride or thionyl chloride [1]. These violent reactions are explained in terms of exothermic polymerisation of formaldehyde produced under a variety of conditions by interaction of the sulfoxide with reactive halides, acidic or basic reagents [2]. Oxalyl chloride reacts explosively with DMSO at ambient temperature, but controllably in dichloromethane at —60°C [3]. See Carbonyl diisothiocyanate, and Dinitrogen tetraoxide, and Hexachlorocyclo-triphosphazine, and Sodium hydride, all below See Perchloric acid Sulfoxides... 

Tris(morpholine)selenonium fluoride (33), easily prepared by the reaction of JV-trimethylsilylmorpholine (34) with selenium tetrafluoride (35), is a very useful reagent for chloride/fluoride exchange reactions (121. Thus, benzenesulfonyl chloride (36) and diphenylphosphinyl chloride (37) gave upon treatment with 33 the corresponding fluorides 38 and 39 in good yields (Scheme 5). 

Sulfonic acids are converted to the corresponding acid halides in much the same way as carboxylic acids. Thionyl chloride is the best reagent for the preparation of methanesulfonyl chloride (83%). By heating with a large excess of thionyl chloride, however, p-toluenesulfonic acid is converted into its anhydride (87%). Benzenesulfonyl chloride is made in 80% yield by the action of either phosphorus pentachloride or phosphorus oxychloride at 180° on sodium benzenesulfonate. Chlorosulfonic and fluorosulfonic acids are used in the conversion of sodium p-chloro-benzenesulfonate to the corresponding sulfonyl halides (85 8S>%). ... 

This cleavage reaction can be performed with a host of reagents phosphorous pentachloride, benzenesulfonyl chloride, phosphoric acid, thionyl chloride, phosphonitrile dichloride, and dichlorocarbene. All these reactions, nevertheless, use conceptually the very same construction of an ester followed... 

Kogay has added many other, somewhat more complicated reagents to the conjoining bond, e.g. diethyl malonate, p-toluenesulfonamide, and aniline benzenesulfonyl chloride and p-tosyl chloride pyridine and iodine afford addition of iodine and a pyridinium iodide group to the bond , mercuric acetate in ethanol in the presence of chloride ion affords addition of HgCl and an ethoxy group. A recent review includes a discussion of the reactions of 1,3-dehydroadamantane . 

From the fact that such diverse reagents as phosphorus pcntarldoride, benzenesulfonyl chloride, sulfuric acid, and chloral have been emptied as reagents for the reaction, it is evident that no single compound could be an intermediate in the reaction. Chloroiinido ketones such as CIV and CV do not appear to be necessary intermediates in the reaction... 

PrtpavtioH. The reagent is readily available by reaction of benzenesulfonyl chloride with silver cyanate or fiom benzenesulfonamide and phosgene. ... 

Paquette found the usual reagents (dimethyl sulfate, benzenesulfonyl chloride-pyridine) ineffective for conversion of the amide function of 1,3-dihydro-3,5,7-trimethyl-2H-azepinone-2 (6) into an imino derivative but that this conversion was effected readily with triethyloxonium fluoroborate to give the 3H-azepine (7). 

Preparation. The reagent is prepared by the reaction of excess sodium azide in water-ethanol with benzenesulfonyl chloride. In an early procedure the latter reagent was dissolved in ethanol before addition to the sodium azide solution.1 In a more recent preparation, benzenesulfonyl chloride is added directly to the ethanolic solution of sodium azide.2... 

Phenyl-1,4-benzoxazepin-5-one (36) was readily acylated with mesyl and benzenesulfonyl chlorides to give the corresponding IV-acylated derivatives. Conversion of the amide to thione (37) was also carried out by the use of Lawesson s reagent (Scheme 14) <93AP(326)73>. 

The tosylation of carbon can be accomplished using electron transfer conditions. Treatment of styrene and analogs with Copper(II) Chloride and tosyl chloride or Benzenesulfonyl Chloride results in a formal replacement of the vinyl proton by the sulfonyl moiety (eq 35). The intermediacy of a trans-(S-chloro sulfone has been demonstrated by H NMR. Treatment with base induced the elimination of HCl. A variety of other sulfonyl transfer reagents can be ertployed in the synthesis of isolated /3-chloro sulfones, with good results (60-97% yield) for a variety of alkenes (ethylene, 1-butene, 2-butene, 1-octene, acrylonitrile, methyl acrylate, and 1,3-butadiene). ... 

Handling, Storage, and Precautions by analogy to benzenesulfonyl chloride, benzenesulfonyl bromide should be assumed to be an irritant and harmful by skin absorption and ingestion. Benzenesulfonyl bromide is best used immediately following preparation and may be used in situ. The reagent is moisture sensitive and will react with nucleophilic solvents (e.g. alcohols), liberating HBr and therefore should be stored under an inert atmosphere. Use in a fume hood. 

Related Reagents. ferf-Butylsulflnyl Chloride Di-teri-butyl Disulfide Benzenesulfonyl Chloride Methanesulfonyl Chloride 2-Nitrobenzenesulfonyl Chloride 4-Nitrobenzenesulfonyl Chloride 2,4-Dinitrobenzenesulfonyl Chloride. ... 

Analysis of Reagent Purity mp, NMR, combustion analysis. Preparative Methods )V-cyclohexylbenzenesulfonamide can be prepared by addition of benzenesulfonyl chloride to a solution of cyclohexylamine in pyridine and purified by recrystallization from ethanol. TV-Chlorination is accomplished by treating a solution of TV-cyclohexylbenzenesulfonamide in dichloromethane with NaOCl solution at 0°C followed by dropwise addition of glacial acetic acid. Alternatively, a suspension of W cyclohexylbenzenesulfonamide in acetic... 

Related Reagents. 2-Nitrobenzenesulfonyl Chloride 4-Nitro-benzenesulfonyl Chloride Nitrobenzenesulfonatnide Benzene-sulfonyl Chloride. 

Related Reagents. Benzenesulfonyl Chloride 4-Bromoben-zenesulfonyl Chloride Mesitylenesulfonyl Chloride p-Toluene-sulfonyl Chloride. 

Preparative Methods the title reagent can be prepared in one step by the reaction of polystyrene-supported benzenesulfonyl chloride (100-200 mesh, available from Aldrich, 51,623-6 [163894-16-4], as 1% DVB cross-linked polystyrene resin with a loading of 1.5-2.0 mmol/g) with sodium azide (1.5 equiv) in DMF/H2O (reaction complete at rt in 16 h). 

Reagents and Equipment. Weigh and place in a 10-mL Erlenmeyer flask 400 mg (1.39 mmol) of the p-(2,2,2-trifluoroacetamido)benzenesulfonyl chloride, which was prepared in Experiment [C2], In a 10 x 75-mm test tube, prepare a solution of 0.6 mL of fresh, concentrafed aqueous ammonia (ammonium hydroxide) and 0.4 mL of deionized wafer. Add this solution to the solid sulfonyl chloride in the Erlenmeyer flask. Now add a boiling stone. Use a glass rod to break up any lumps of the solid that may form. 

Benzenesulfonyl chloride pyridine Cyclic ethers from diols s. 7, 355 stereospecific ring closure, tetrahydrofurans, C OH also with f. reagents, and from dimesylates preferably with NaOH, s. M. L. Mihailovid, S. Gojkovic, and 2. Cekovic, Soc. Perkin I 1972, 2460... 

Fridkin et al. (1971) have employed polymeric benzenesulfonyl chloride as a coupling reagent for peptide synthesis via the polymeric mixed... 

Radical Addition Reactions of Vinyltrimethylsilane. Reaction of the title reagent with benzenesulfonyl chloride under radical addition conditions provides ( )-l-phenylsulfonyl-2-trimethylsilylethylene (15), an acetylene equivalent in Diels-Alder reactions (eq 8). In similar fashion, thiophenol adds to vinyltrimethylsilane regioselectively.i Oxidation of the thiophe-... 

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