Disulfide, diphenyl

Alternative synthetic routes to poly(arylene sulfide)s have been pubHshed (79—82). The general theme explored is the oxidative polymerization of diphenyl disulfide and its substituted analogues by using molecular oxygen as the oxidant, often catalyzed by a variety of reagents ... 

Benzisothiazoles are formed by the action of ammonia or amines on benzenesulfenyl halides bearing an o-carbonyl function (72AHC 14)43, 80MI41700). Analogous diphenyl disulfides behave similarly (77SST(4)339). Sulfinyl chlorides or phenylsulfoxides produce... 

Diphenyl disulfide (phenyl disulfide) [882-33-7] M 218.3, m 60.5 . Crystd from MeOH. [Alberti et al. J Am Chem Soc 108 3024 1986]. Crystd repeatedly from hot diethyl ether, then vac dried at 30° over P2O5, fused under nitrogen and re-dried, the whole procedure being repeated, with a final drying under vac for 24h. Also recrystd from hexane/EtOH soln. [Burkey and Griller 7 Am Chem Soc 107 246 1985.]... 

Diphenylcyclopropenone, 47, 62 Dii henyldiacetylene, 45, 39 Diphenyl disulfide, oxidation to methyl benzenesulfinate, 46, 62 1,1-Diphenylethylene, reaction with N,or diphenylmtrone, 46,129 N,N -Diphi iiyli tiiyleni diamine, condensation with triethyl orthoformate, 47, 14... 

The asymmetrical anhydrobase (20) constitutes the first step of the formation of trimethine thiazolocyanine when a 2-methylthiazolium salt reacts either with a benzothiazolium or its opened form [which is bis-o-(formylmethylamino)(diphenyl disulfide] (Scheme 26). In a second step, 20 is protonated by a second molecule of 2-methylthiazolium. It results in cleavage of the benzothiazoline ring, which gives 21 together with the formation of the monomeric anhydrobase (22). Cleavage of the C-S bond of 20 can be explained by the important electronic desaturation of the C atom observed in NMR spectrum and the great polarizability of the C-S bond in this type of ring (48). 

Dicyclopentadienyltin also takes part in oxidative addition reactions with such reagents as iodomethane, diiodomethane, ethyl bromoace-tate, and diphenyl disulfide, and there is evidence that the reactions involve a radical chain-mechanism (324, 325). 

Fig. 67. Conversion of thioplienol to diphenyl disulfide by MoiCo2(/i3-S)4(CO i(ip -C H4H02. ...

Trimethylsilyl esters of tris(thio)phosphonic acids 2070 are readily oxidized by DMSO in toluene at -30 °C to give the dimeric tetra(thia)diaphosphorinanes 2071 and HMDSO 7 [208] (cf. also the oxidation of silylated thiophenol via 2055 to diphenyl disulfide). The polymeric Se02 is depolymerized and activated by reaction with trimethylsilyl polyphosphate 195 to give the corresponding modified polymer... 

A metal-iodine exchange has been carried out on all three diazine systems under very mild conditions using lithium tri- -butyl magnesate, although only one substrate from each system was used 3-iodo-6-phenylpyridazine, 4-iodo-2-methylthiopyrimidine and 2-iodopyrazine. The pyridazine example was most problematic, possibly due to solubility problems. Aldehydes, benzophenone and diphenyl disulfide were used as the electrophiles <06SL1586>. 

Thianthrene and diphenyl disulfide show no detectable paramagnetic resonance absorption in inert solvents, but appear to dissociate somewhat in sulfuric acid solution.78... 

As with other haloaromatic systems, Barbier reactions are also suitable for heterocyclic systems. For example, the lithio derivatives formed in situ from iodide 187 upon sonication reacted immediately with electrophiles such as benzaldehyde, hexanal and diphenyl disulfide, to give good yields of 188 <00T3709>. Similar chemistry was also successful with pyrazines, pyrimidines, and pyridazines. 

Addition of diphenyl disulfide (PhS)2 to terminal alkynes is catalyzed by palladium complexes to give l,2-bis(phe-nylthio)alkenes (Table 3)168-172 The reaction is stereoselective, affording the (Z)-adducts as the major isomer. A rhodium(i) catalyst system works well for less reactive aliphatic disulfides.173 Bis(triisopropylsilyl) disulfide adds to alkynes to give (Z)-l,2-bis(silylsulfanyl)alkenes, which allows further transformations of the silyl group to occur with various electrophiles.174,175 Diphenyl diselenide also undergoes the 1,2-addition to terminal alkynes in the presence of palladium catalysts.176... 

Addition of disulfides to carbon-carbon double bonds is catalyzed by ruthenium complexes (Equation (71)).204 Even relatively less reactive dialkyl disulfides add to norbornene with high stereoselectivity in the presence of a catalytic amount of Cp RuCl(cod). Diphenyl disulfide adds to ethylene and terminal alkenes under identical conditions (Equation (72)). 

Addition of diphenyl disulfide to various alkenes is promoted also by GaCl3 at 0°C (Equation (75)).186... 

Diphenylcyclopropane, 48, 75 Diphenylcyclopropenone, 47, 62 Diphenyldiacetylene, 46,39 Diphenyl disulfide, oxidation to methyl... 

Diphenyl-1,3-butadiene, 40, 36 Diphenylcarbodiimide, 43,31 Diphenyl disulfide, set Phenyl disulfide Diphenyl ketimine, 44, 51 Diphenylmethylenimine, 44, 51 oe,j8-DlPHENYLPROPIONIC ACID, 40, 38 Dipotassium l, 8-naphthalenedicarbox-... 

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