Potassium thiophenolate

Reaction of the photobromination product 40 of tri-<9-acetyl-1,6-anhy-dro-/ -D-glucopyranose under conditions of kinetic control gives mainly the c rfo-products of displacement with inversion of configuration thus, potassium thiophenolate affords compound 142 in 73% yield, and methanolysis... 

Suzuki-Miyaura coupling of D with I smoothly afforded J, which was oxidized with ceric ammonium nitrate to give K. For the final demethylation of K, several methods were tried without success treatment of K with boron tribromide, 47% hydrobromic acid, lithium chloride in DMF, trimethylsilyl iodide, and potassium thiophenolate in diethylene glycol. Finally, clean demethylation of K was achieved with aluminum chloride in dichloromethane at room temperature to give diospyrin (58) as orange plates. The proposed structure 58 was thus confirmed by its synthesis.130... 

In anionic ring-opening polymerization of cyclopropane-1,1-dicarboxylates 22 using sodium and potassium thiophenolates as initiators, the nature of the cation was found to play an important role in the rate and selectivity of the polymerization. In particular, reaction rate increased in the order Na < C DCH18C6]... 

Aromatic sulphinic acids are oxidised by potassium permanganate.to sulphonio acids and are reduced by zinc and hydrochloric acid to thiophenols. 

Butyroin has been prepared by reductive condensation of ethyl butyrate with sodium in xylene, or with sodium in the presence of chloro-trimethylsilane. and by reduction of 4,5-octanedlone with sodium l-benzyl-3-carbamoyl-l,4-dihydropyridine-4-sulfinate in the presence of magnesium chloride or with thiophenol in the presence of iron polyphthalocyanine as electron transfer agent.This acyloin has also been obtained by oxidation of (E)-4-octene with potassium permanganate and by reaction of... 

In an attempt to protect thiophenols during electrophilic substitution reactions on the aromatic ring, the three substituted thioethers were prepared. After acetylation of the aromatic ring (with moderate yields), the protective group was converted to the disulfide in moderate yields, 50-60%, by oxidation with hydrogen peroxide/boiling mineral acid, nitric acid, or acidic potassium permanganate. ... 

Positional changes of the exocyclic oxygen atom in 157b and 158b discriminate between the reactivity of these compounds. Thus, 158b readily reacts with the potassium salt of thiophenol to give sulfide 177 in 85% yield (83JHC783),... 

Thiophenols may also be synthesized via the photochemical decomposition route 156). Thus, treatment of arylthallium ditrifluoroacetates with an aqueous solution of potassium Ar,AT-dimethyldithiocarbamate led in quantitative yields to the formation of the corresponding aryl AT,A -dimethyl-dithiocarbamates. Subsequent photolysis in aqueous acetone then led to disulfides which were reduced to the thiophenols. A small amount of aryldithiocarbamate formed as a by-product in the photolysis was converted to the same thiophenol by hydrolysis. The overall reaction sequence is illustrated in Eq. (18). 

A-Protected amines were assembled on solid-phase via sulfonamide-based handle 58 (Scheme 27) [67]. Tertiary sulfonamides were generated upon reaction with allylic, benzylic and primary alcohols under Mitsu-nobu conditions. Secondary amines were released from the support using mild nucleophilic conditions such as treatment with thiophenol and potassium carbonate. 

It is synthesized by reaction of the diazonium salt from amine 1 with potassium ethyl xanthate, followed by alkaline hydrolysis to afford thiophenol 2. 

Dining preparation of thiophenol by addition of a cold solution of potassium O-methyldithiocarbonate to a cold solution of benzenediazonium chloride, a violent explosion accompanied by an orange flash occurred [1], This was attributed to the formation and decomposition of bis(benzenediazo) disulfide. A preparation in which the diazonium solution was added to the xanthate solution proceeded smoothly [2],... 

In the case of thiol and inorganic salts, the best result was obtained for thiophenol and sodium cyanide, and DS of 90% was attained (60°C) with minimum amounts of C=C formation even for p-thiocresol (equivalent) and potassium carbonate. 

The reaction of o,p-dicyano-a-phenylsulphonyl cumene with sodium thiophenolate in DMF produces o,p-dicyano-a-phenylthiocumene. A product of similar substitution is obtained with the potassium salt of diethyl malonate as a reactant (Komblum and Fifolt 1980 Scheme 4.1). 

Thiophenol and potassium hydroxide were purchased by the submitters from Tokyo Kasei Kogyo Co. and by the checkers from Aldrich Chemical Company, Inc. and Mallinckrodt Inc., respectively. 

A similar mechanism is thought to be involved when functionalized dihalocyclopropanes are treated with sodium alkoxides as well as thiophenolates or subjected to the influence of potassium hydroxide in methanol. 

Some strategies used for the preparation of support-bound thiols are listed in Table 8.1. Oxidative thiolation of lithiated polystyrene has been used to prepare polymeric thiophenol (Entry 1, Table 8.1). Polystyrene functionalized with 2-mercaptoethyl groups has been prepared by radical addition of thioacetic acid to cross-linked vinyl-polystyrene followed by hydrolysis of the intermediate thiol ester (Entry 2, Table 8.1). A more controllable introduction of thiol groups, suitable also for the selective transformation of support-bound substrates, is based on nucleophilic substitution with thiourea or potassium thioacetate. The resulting isothiouronium salts and thiol acetates can be saponified, preferably under reductive conditions, to yield thiols (Table 8.1). Thiol acetates have been saponified on insoluble supports with mercaptoethanol [1], propylamine [2], lithium aluminum hydride [3], sodium or lithium borohydride, alcoholates, or hydrochloric acid (Table 8.1). 

Thiophenol, 2,4,6-Trinitro (2,4.6-Trinitro-phenylmercaptan or Picrylmercaptan). C6H3N3S06 mw 245.18 N 17.14% OB to C02 —48.94% v small yel ndls with a bitter taste mp 114° v sol in acet, benz, chlf, ethanol and w insol in carbon disulfide and petr eth. Prepn is by reacting an ethanolic soln of K2S with an ethanolic soln of picryl chloride. The K salt formed is filtered off and dissolved in w and then hydrolyzed with hydrochloric acid to the free nitrate. The picryl compd explds with extreme violence at 115°. The salt, Potassium-2,4,6-Trinitro-Thiophenol KC6H2N3S06 mw 283.27 N 14.84% OB to C02 -48.94% reddish brn ndls v sol in ethanol and w difficultly sol in eth and w mp, explds with great violence at 140°... 

Benzofuro[3,2-b] [ 1,5]benzothiazepine (137) was obtained from 2-amino-thiophenol (5) and 3-chloro-2-formyl-6-methoxybenzofuran (136) in acetonitrile containing potassium carbonate (Scheme 42) (87MI1). 

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