Toluene sulfonyl chloride

D-Campbor-IO-snlfonyl chloride 2-Metbylbe zenesulfonyl cbloride (Toluene-2-sulfonyl chloride) Naphlhalene-I-sulfonyl chloride 4-Methylbenzenesulfonyl chloride (Toluene-4 Sulfonyl chloride)... 

Toluene-2-sulfonyl chloride is converted into the corresponding sulfonamide, which, after an oxidation step, is used in the production of the sweetener saccharin. 

Toluene-2-sulfonyl chloride Toluene-4-sulfonyl chloride... 

Pivalates. The selective pivaloylation of sucrose with pivaloyl (2,2-dimethylpropionyl) chloride has been thoroughly investigated (56). The reactivity of sucrose toward pivaloylation was shown to be significantly different from other sulfonic or carboxyflc acid chlorides. For example, reaction of sucrose with four molar equivalent of toluene-/)-sulfonyl chloride in pyridine revealed, based on product isolation, the reactivity order ofO-6 0-6 > 0-1 > 0-2 (57). In contrast, a reactivity order for the pivaloylation reaction, under similar reaction conditions, was observed to be 0-6 0-6 > 0-1 > 0-4. 

In this method, an oligoethylene glycol is treated with 0.3 eq. of sodium bromoace-tate in methanol. The resulting monocarboxylic acid salt is then treated with toluene-sulfonyl chloride, sodium carbonate and dioxane. After heating the reaction mixture at 50° for an hour, the product was obtained either by Kugelrohr distillation or extraction. The two compounds produced in the reaction below (i.e., n = 1 and n = 2) were formed in 38% and 42% yields respectively . 

The aromatic sulfonyl chlorides which have no a-hydrogen and thus cannot form sulfenes give acylic sulfones. Thus 1-piperidinopropene on reaction with benzene sulfonyl chloride (9J) gave 2-benzenesulfonyl-l-piperidinopropene (153). Similarly the enamine (28) reacts with p-toluene-sulfonyl chloride to give the 2-p-toluenesulfonylcyclohexanone (154) on hydrolysis (/OS). 

Qi-Hydroxy-17-methyltestosterone p-Toluene sulfonyl chloride Hydrogen fluoride... 

Methyl a-D-mannopyranoside was treated in succession with p-toluene-sulfonyl chloride, carbonyl chloride, and benzoyl chloride, and, without isolating the intermediates, there was obtained in 37% yield methyl 4-0-l enzoyl-2,3-O-carbony 1-6-0-(p-tolylsulfonyl ) -D-mannoside. The tos-yloxyl group of the latter was replaced by iodine, and hydrogenation of the 6-iodo derivative in the presence of a nickel boride catalyst gave methyl 4-0-benzoyl-2,3-0-carbonyl-6-deoxy- -D-mannoside. Treatment of the latter with hydrogen bromide in acetic acid gave crystalline 4-0-benzoyl-2,3-0-carbonyl-6-deoxy-a-D-mannosyl bromide (8) (16). The... 

Whereas aryl Grignard compounds afford good yields of sulfones with sulfonyl fluorides298 299, phenyllithium is mainly chlorinated by a-toluene-sulfonyl chloride on the other hand, the corresponding fluoride yields only a trace of the expected mono-sulfonylation product, while the main product is 26 obtained by twofold sulfonylation300 (equation 61). 

Chloroethyl)polystyrenes and (iodoethyl)polystyrenes are each prepared from the alcohol by common reagents in a single step without complications, but one-pot procedures fail to produce completely pure bromide, which must be prepared from the tosylate by assisted halide exchange (57). The preparation of (toluenesulfonyloxyethyl)polystyrene itself, if performed in ice-cold pyridine as for the free analogue (64, 65), required a week to complete (67) if quaternary ammonium and other side-products (68) are to be avoided. In contrast, with non-nucleophilic diisopropylamine (69) as acid acceptor instead of pyridine, (hydroxyethyl)polystyrene and toluene-sulfonyl chloride need only be refluxed in carbon tetrachloride for a few hours to give the desired tosic ester as sole product in quantitative yield (57). 

Figure 8 Partial MALDI-TOF spectrum from PMMA generated by ATRP with p-toluene sulfonyl chloride as initiator (inset shows theoretical isotope distribution for lithiated 13-mer of 6). (Peak labelled 7 arises from post-source decay of 7 [10].)...

This procedure represents the most convenient synthesis of 3(5)-aminopyrazole. It employs readily available starting materials and gives excellent yields in all steps.5,6 />-Toluene-sulfonyl chloride can be replaced by other arenesulfonyl chlorides. 3-Imino-l-arylsulfonylpyrazolidines can be alkylated with dimethyl sulfate or with alkyl 7>-toluenesulfonates in dimethyl-formamide to give salts of l-alkyl-2-arylsulfonyl-5-amino-4-... 

Not every substitution of alkanesulfonyl chlorides, by any means, involves an elimination—addition mechanism. Thus, while the reactions of cr-toluene-sulfonyl chloride, PhCH2S02Cl, with either hydroxide ion, or primary and... 

Chen, G.C. (1992a). Fungal resistance of loblolly pine reacted with para-toluene, sulfonyl chloride or isocyanate. Wood and Fiber Science, 24(2), 161-167. 

Automated parallel experiments were carried out to rapidly screen and optimize the reaction conditions for ATRP of methyl methacrylate (MMA) [34]. A set of 108 different reactions was designed for this purpose. Different initiators and different metal salts have been used, namely ethyl-2-bromo-tTo-butyrate (EBIB), methyl bromo propionate (MBP), (1-bromo ethyl) benzene (BEB), and p-toluene sulfonyl chloride (TsCl), and CuBr, CuCl, CuSCN, FeBr2, and FeCl2, respectively. 2,2 -Bipyridine and its derivatives were used as ligands. The overall reaction scheme and the structure of the used reagents are shown in Scheme 2. 

N 12.50%, OB to CO2 -74.0%, crysts (benz), mp 136.5-137.0°. Prepd by heating p-toluene-sulfonyl chloride with trinitroethanol and a trace of pyridine... 

One Sanofi synthesis of enantiomerically pure (-i-)-clopidogrel (2) utilized optically pure (R)-(2-chloro-phenyl)-hydroxy-acetic acid (20), a mandelic acid derivative, available from a chiral pool. After formation of methyl ester 21, tosylation of (/ )-21 using toluene sulfonyl chloride led to a-tolenesulfonate ester 22. Subsequently, the Sn2 displacement of 22 with thieno[3,2-c]pyridine (8) then constructed (-i-)-clopidogrel (2). Another Sanofi synthesis of enantiomerically pure (-i-)-clopidogrel (2) took advantage of resolution of racemic a-amino acid 23 to access (S)-23. The methyl ester 24 was prepared by treatment of (S)-23 with thionyl chloride and methanol. Subsequent Sn2 displacement of (2-thienyl)-ethyl para-toluene-sulfonate (25) assembled amine 26. 

Tr in itro-2,4-dicblorobenzene or 2,4,6-Trinitro-l,3mdichlorobenzene, col prisms (from ale), mp 129° was prepd by heating 2,4,6ftrinitro-3-chlorophenol with p-toluene-sulfonyl chloride 81 N,N-diethylaniline and by other methods (Refs 1 2)... 

The rates of reaction of diisopropylidene derivatives of L-sorbose, D-glucose and D-galactose with an excess of triphenylmethyl chloride in pyridine, have been studied.162 Similar studies were then conducted on the reactivity of these diisopropylidene derivatives with p-toluene-sulfonyl chloride.168... 

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