Arylsulfonation

Mocimycin has been chemically converted to aurodox by protection of the 4-hydroxy group at the pyridone moiety as the benzoylformate, followed by /V-methylation and hydrolytic removal of the protective group (1,55). Whereas aurodox esters are active growth promotors in animals, goldinamines that are A/-acylated by acids other than goldinonic acid, such as acetic, benzoic, or arylsulfonic acids, lack useful antimicrobial or growth-promoting activity (1). 

Fusion/Hydroxylation. The conversion of arylsulfonic acids to the corresponding hydroxy compound is normally effected by heating with caustic soda (caustic fusion). The primary examples are P-naphthol in the naphthalene series and resorcinol in the benzene series further examples are m- am in oph en o1 from metanilic acid and diethyl-y -arninophenol from /V,/V-diethy1metani1ic acid. In the naphthalene series the hydroxy group is much... 

The nitrene can be generated by a variety of methods, the most popular being the thermal or photolytic decomposition of azidoformates. Other methods, particularly the base-catalyzed a-elimination of arylsulfonate ion from 7V-[(arylsulfonyl)oxy]urethanes, are useful as they avoid the use of the potentially explosive azido esters. 

These compds are also formed during the prepn of nitriles, by heating aryl or arylalkyl halides, or alkyl sulfuric or phosphoric esters, or arylsulfonic esters with K or Na cyanide in ale... 

D. Arene Sulfonate-Arylsulfone (Sulfone-Fries) Rearrangement.171... 

Diaryl sulfones can be formed by treatment of aromatic compounds with aryl sulfonyl chlorides and a Friedel-Crafts catalyst. This reaction is analogous to Friedel-Crafts acylation with carboxylic acid halides (11-14). In a better procedure, the aromatic compound is treated with an aryl sulfonic acid and P2O5 in polypho-sphoric acid. Still another method uses an arylsulfonic trifluoromethanesulfonic anhydride (ArS020S02CF3) (generated in situ from ArS02Br and CF3S03Ag) without a catalyst. ... 

It is evident from the foregoing sections that simple alkylvinyl halides do not react via an Sn 1 mechanism, if at all, even under extreme solvolytic conditions (146,149). More reactive leaving groups, such as arylsulfonates, were clearly needed to investigate the possible solvolytic behavior of simple alkylvinyl systems, but the preparation of vinyl sulfonates until recently was unknown. Peterson and Indelicato (154) were the first to report the preparation of vinyl arylsulfonates via reaction of the appropriate disulfonate with potassium t-butoxide in refluxing f-butanol. They prepared and investigated the solvolysis of 1-cyclohexenyl tosylate 169 and c/s-2-buten-2-yl tosylate 170 and the corresponding p-bromobenzenesulfonates (brosylates). Reaction... 

Biedlingmeier JJ, A Schmidt (1983) Arylsulfonic acids and some 5-containing detergents as sulfur sources for growth of Chlorellafusca. Arch Microbiol 136 124-130. 

Junker F, AM Cook (1997) Conjugative plasmids and the degradation of arylsulfonates in Comamonas testos-teroni. Appl Environ Microbiol 63 2403-2410. 

Alkyl- and arylsulfonates, e.g., aethane- or heptanesulfonate, caaphorsulfonic acid... 

Table 10-1. Arylsulfonates from 1 -arylsulfonyl-3-methylimidazolium triflate.

Oligonucleotides with Arylsulfonic Azolides (Arylsulfonylazoles) as Condensing Agents... 

Imidazolides, 1,2,4-triazolides, or tetrazolides of arylsulfonic acids have been used as condensing agents in expedient syntheses of oligodeoxynucleotides. 

Oligonucleotides with Arylsulfonic Azolides as Condensing Agents 331... 

Instead of the isolated arylsulfonic acid azolides, mixtures of arylsulfonic acid chlorides and azoles have also been used for phosphorylation on a nucleoside 5 -OH or as coupling agents in the synthesis of oligodeoxyribonucleotides. 94 133 1371... 

Layered zinc arylsulfonates can be prepared from sodium arvlsulfonate in the presence of zinc salts. Some compounds have been structurally characterized.4... 

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