P sulfones

Benzyl toluene-p-sulfonate [1024-41-5 M 162.3, m 58 . Crystd from pet ether (b 40-60°). 

Sodium p-hydroxyphenylazobenzene-p -sulfonate [2623-36-1] M 288.2. Crystd from 95% EtOH. 

Methylation of 2- or 4-methylquinazoline is reported to proceed with difficultyj" but 4-methylquinazoline has been quaternized with methyl iodide. The product was very hygroscopic and, although not purified, was shown to consist mostly of 1,4-dimethylquinazolinium iodide, since it gave the same cyanine dye (11) with 2-methylthio-benzthiazole metho-toluene-p-sulfonate as did l-methyl-4-methyl-thioquinazolinium iodide (of unambiguous structure) with 2-methyl-benzthiazole methiodide. ... 

Although the uses of dimethyl sulfate and methyl toluene-p-sulfonate are well known, in many cases these reagents have been used in solution, e.g. in nitrobenzene, in addition to the older... 

R = H, R" = NHAc) reacts with methyl toluene-p-sulfonate at 120°-l 30° to yield a quaternary salt which is thought to be 147 (R = H, R = NHAc) reaction is believed to occur at N-1 in spite of the proximity of the hydrogen atom in the 10-position. ... 

The formation of quinoxaline quaternary salts is often difficult. However, reaction of quinoxaline with ethyl iodide in boiling acetonitrile gives ethyl quinoxalinium iodide in 76% yield, and treatment of the parent base with methyl toluene-p-sulfonate at room temperature gives methyl quinoxalinium toluene-p-sulfonate in quantitative yield. ... 

Treatment of 2-aminoquinoxaline with methyl toluene-p-sulfonate at G. W. H. Cheeseman, unpublished work. 

Suitably substituted azo compounds constitute an important class of dyes—the azo dyes. Some derivatives such as /j-dimethylaminoazobenzene- p -sulfonic acid Na-salt (trivial name methyl orange) are used as pH-indicators. 

Cu(H03SC6H4C2N5H5)2] Copper (II) complexes of 1-phenylbiguanide-p-sulfonic acid, 7 6 Cul, 6 3... 

The first application of microwave irradiation in conjunction with dry media in the generation of nitrile oxide intermediates was reported by Hamelin [29]. In this example, methyl nitroacetate (170) was mixed with a dipolarophile in the presence of catalytic amounts of toluene-p-sulfonic acid (PTSA) (10% weight). Subsequent microwave irradiation led to the formation of the corresponding heterocyclic adducts (Scheme 9.52). Reactions were performed in an open vessel from which water was continuously removed [103], Likewise, irradiation in a domestic oven of a mixture of ethyl chloro(hydroxyimino)acetate (173) and a dipolarophile over alumina led to the same results in only a few minutes (Scheme 9.52) [103]. 

The rate constants k and ku for la calculated from the data in Fig. 14 of ca. 3.5 x 103 and 1.5 x 104M 1s 1 (pH 11, 25°C), respectively, illustrate a very high activity of Fe-TAML activators particularly in terms of k. For example, Oakes and Gratton reported the value of 0.08M s1 for the oxidation of Orange II by p-sulfonated perbenzoic acid under the same conditions (57). 

Butyl butyrate, 4 460 p- -Butylcafix[4]arene, 14 165 4- -Butylcalix[8]arene-p-sulfonic acid, 23 722 D-re-Butyl carbonate, physical properties, 6 306t... 

Use of the water-soluble analogues of complexes 90 and 91 were later reported by Williams and coworkers [83]. In this study, water solubility was achieved by replacing the chiral diamines TsDPEN and TsCYDN with the p-sulfonated derivatives TsDPEN-S03Na and TsCYDN-S03Na (Scheme 4.41). The ATH of aryl alkyl... 

Janus [11] has recently shown that urea can also be smoothly methylated with methyl toluene-p-sulfonate at 80°-90°C to give good yields of crystalline 2-methylpseudourea toluene-p-sulfonate. 

To a solution of 1.5 gm (0.0104 mole) of j8-naphthol in 100 ml of dry benzene containing 1.7 ml of dry pyridine maintained at 55°C is added a solution of 4.3 gm (0.103 mole) of p-n-decyloxybenzenediazonium toluene-p-sulfonate in 50 ml of dry benzene maintained at 60°C. The mixture is kept overnight. Then the precipitated pyridinium toluene-p-sulfonate is filtered off. The filtrate is cautiously evaporated to dryness. On recrystallization of the residue from ethanol, 3.4 gm of l-(p- -decyloxyphenylazo)-2-naphthol is isolated, m.p. 73°-76°C, yield 85 %. On further recrystallization the melting point may be raised to 78°-79°C. 

Orthoesters. The value of cyclic orthoesters as intermediates for selective acylation of carbohydrates has been demonstrated (73). Treatment of sucrose with trimethylorthoacetate and DMF in the presence of toluene-p-sulfonic acid followed by acid hydrolysis gave the 6-0-acetylsucrose as the major and the 4-0-acetylsucrose [63648-80-6] as the minor component. The latter compound underwent acetyl migration from C-4 to C-6 when treated with an organic base, such as / -butylamine, in DMF to give sucrose 6-acetate in >90% yield (74). When the kinetic reagent 2,2-dimethoxyethene was used,... 

The most widely applicable method for synthesis of unsymmetrically substituted dipyrrylmethanes (129) requires the condensation of a 2-unsubstituted pyrrole (124) with a 2-acetoxymethylpyrrole (128). This reaction was originally carried out with sodium acetate in hot acetic acid (60JA4389), but subsequent developments have shown that the conditions can be much milder if a catalytic quantity of toluene-p-sulfonic acid (in warm methanol or acetic acid) is employed (73JCS(Pl)247l). 

Finally may bo cited two examples from steroid chemistry, involving diaxial ting opening of 2a,34z-epoxy steroids (Eq. 784) and 2 ,30-epoxy steroids (Eq. 783) with toluene-p-sulfonic acid.l5W Many... 

Tartrazine was separated from the intermediates sulfanilic acid, pyrazolone-T, and phenyl-hydrazine-p-sulfonic acid (PHSA) and from the side reaction products DAADBSA and l-(4-sulfophenyl)-3-ethyl carboxy-5-hydroxypyrazolone (EEPT) by ion-exchange HPLC (199,214). 

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