Sulfides aryl phenyl

SULFIDE SYNTHESIS IN PREPARATION OF DIALKYL AND ALKYL ARYL SULFIDES NEOPENTYL PHENYL SULFIDE... 

HEXAHYDRO - 4a,5 - DIMETHYL - 2(3H) - NAPHTHALE-NONE and 2-TRIMETHYLSILYLOXY-1,3-BUTADIENE AS A REACTIVE DIENE DIETHYL trans -4-TRIMETHYL-SILYLOXY-4-CYCLOHEXENE-1,2-DICARBOXYLATE. Sulfur substitution also continues to be of high interest, and three preparations on sulfide synthesis are included BENZYL SULFIDE DIALKYL AND ALKYL ARYL SULFIDES NEOPENTYL PHENYL SULFIDE and UNSYMMETRICAL DIALKYL DISULFIDES sec-BUTYL ISOPROPYL DISULFIDE. 

Aryl iodides react with benzenethiolate ions in liquid ammonia under irradiation to afford aryl phenyl sulfides in good yields [51,54—59]. 

Several DNA and RNA pyrimidine nucleobase radicals have been generated from ketone precursors by the Norrish type I cleavage, aryl sulfides and phenyl selenides (Scheme 35). Formal hydrogen atom addition adducts of thymidine (80) and 2 -deoxyuridine (83) have been produced using these types of precursors, as has the C5-thymidine HO adduct (76,... 

The oxo(salen)Mn(V) complex, (8) is the effective oxidant in the Mn(III)salen-catalysed oxidation of aryl phenyl sulfides by hypochlorite in MeCN/H20. First-order dependence on oxidant and sulfide is observed and the rate is reduced by electron-attracting substituents in the sulfides and electron-releasing substituents in salen. The Hammett p-value (-2.16.) determined for substituted sulfides indicates an electron-deficient transition state Hammett correlations for substituted salen complexes give positive /O-values for each sulfide. The substituent-, acid-, and solvent effects indicated direct transfer of the 0-atom from the oxidant to the substrate in the rate-determining step. ... 

A mild and chemoselective oxidation of sulfides to sulfoxides by o-iodooxybenzoic acid (IBX) catalyzed by tetraethylammonium bromide (TEAB) has been reported [73]. The reaction is highly selective, and no overoxidation to sulfone was observed. Simple aryl alkyl sulfides are oxidized in 93-98% yield in 0.3-2 h at room temperature with the use of 5 mol% of TEAB. Diphenyl sulfide and phenyl benzyl sulfide took 30 and 36 h, respectively, to go to completion under these conditions. 

A useful survey of the chemistry of phosphite radicals, prepared by pulse radiolysis, has been presentedThese can take part in oxidation, reduction, substitution, and addition reactions. Reports have been published on the oxidation by peroxodiphosphate of alkyl aryl sulfides,methyl phenyl sulfoxide,and hexacyanoferrate(II). The oxidation of dialkyl sulfides by peroxomonophos-... 

Varying degrees of vitro antifungal activity have been claimed for a variety of chemical types. Among these are substituted 8-hydroxyquino-lines,J 2 acetylenic con5>oun, 3 2-fluorofatty acids,alkyl phenyl sulfides,aryl thiocyanates,substituted phenylhydrazines and phenyl-pyrazolones methyl-5-(3,3-dimethyl-l-triazeno)imidazole- -carboxylate p-hydroxypropiophenone,50 substituted benzimidazoles,51 2,U-bis(arylamino)-5-methylpyrimidines52 and isothiocyanates.53... 

Aryl and alkenyl phenyl sulfides are prepared by the reaction of aryl and alkenyl halides and inflates with tributylstannyl phenyl sulfide. 2-Chloropyrimidine (737) is used for the coupling[606,607]. The diaryl or divinyl sulfide 739 is prepared by the reaction of distannyl sulfide (738)[548], N,N-Diethylaminotributyltin (740) reacts with aryl halides to give arylamines[608]. 

Aryl sulfides are prepared by the reaction of aryl halides with thiols and thiophenol in DMSO[675,676] or by the use of phase-transfer catalysis[677]. The alkenyl sulfide 803 is obtained by the reaction of lithium phenyl sulfide (802) with an alkenyl bromide[678]. 

Other sulfur compounds such as thiourea, ammonium dithiocarbamate, or hydrogen sulfide also lead to 2-mercaptothiazoles. Thus thiourea has been used in the syntheses of 4,5-dimethyl (369) and 4-aryl-2-mercapto-thiazoles (Table 11-30) (519). The reactions were carried out by condensing the ia -thiocyanatoketones with thiourea in alcohol and water acidified with hydrochloric acid. By this procedure, 4-aryl-2-mercaptothiazoles were obtained in yields of 40 to 80% with bis-(4-aryl-2-thiazolyl) sulfides as by-products (519). These latter products (194) have also been observed as a result of the action of thiourea on 2-chloro-4-arylthiazole under the same experimental conditions. They can be separated from 2-mercaptothiazoles because of their different degrees of solubility in sodium hydroxide solution at 5%. In this medium bis-(4-phenyl-2-thiazolyl)sulfide is... 

Early efforts to effect the photoinduced ring expansion of aryl azides to 3H-azepines in the presence of other nucleophiles met with only limited success. For example, irradiation of phenyl azide in hydrogen sulfide-diethyl ether, or in methanol, gave 17/-azepine-2(3//)-thione35 (5% mp 106—107 " O and 2-methoxy-3//-azepine (11 %),2 3 respectively. Later workers194 failed to reproduce this latter result, but found that in strongly basic media (3 M potassium hydroxide in methanol/dioxane) and in the presence of 18-crown-6, 17/-azepin-2(3//)-one was produced in 48% yield. In the absence of the crown ether the yield of azepinone falls to 35%. 

Several alkyl aryl sulfides were electrochemically oxidized into the corresponding chiral sulfoxides using poly(amino acid)-coated electrodes448. Although the levels of enan-tioselection were quite variable, the best result involved t-butyl phenyl sulfoxide which was formed in 93% e.e. on a platinum electrode doubly coated with polypyrrole and poly(L-valine). Cyclodextrin-mediated m-chloroperbenzoic acid oxidation of sulfides proceeds with modest enantioselectivity44b. 

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