Tolyl disulfide

Aminophenyl disulfide Cystine, 2-Nitrophenyl disulfide Methyl disulfide, p-tolyl disulfide Benzyl disulfide Naphthothiophenes (NTH)... 

Similar to 67, the oxanickelacycle 69 prepared from 3-hexyne, Ni(cod)2/bipy, and C02 also acted as a nucleophilic reagent. The reaction of 69 with p-tolyl disulfide took place at the Ni-C bond to give vinyl sulfide 70 in 53% yield after esterification (Scheme 23).37 In the case of 2-bromopropiophenone as an electrophile, the cycloadduct 71 was obtained in 47% yield after acidic workup. 

Di(tolyl) -disulfides or Dimethyl-diphenyl-disulfide and Derivatives... 

Another ready source of a suitable 2-mercaptobcnzaldehyde derivative (12) stems from the Rieche formylation of di-/>-tolyl disulfide (Scheme 9). 

The best evidence for the photolytic decomposition of mercaptans and disulfides into free radicals involves photoinitiation of polymerization of olefins. Thus, photolysis of disulfides initiates the copolymerization of butadiene and styrene,154 as well as the polymerization of styrene207 and of acrylonitrile.19 Thiophenol and other thiols promote polymerization upon ultraviolet irradiation.19 Furthermore, the exchange of RS-groups between disulfides and thiols is greatly accelerated by light. Representative examples are benzothiazolyl disulfide and 2-mercapto-thiazole,90 tolyl disulfide and p-thiocresol, and benzyl disulfide and benzylmercaptan.91 The reaction probably has a free radical mechanism. Similar exchange reactions have been observed of RS-groups of pairs of disulfides have been observed.19... 

When a smaller excess of chlorine is used poorer yields of sulfenyl chloride are obtained, a larger proportion of p-tolyl disulfide being formed. 

This material is suitable for use in further synthesis without purification by distillation, particularly if the presence of a few per cent of />-tolyl disulfide is of no consequence. 

Toluenesulfenyl chloride has been prepared by the action of chlorine on a solution of -toluenethiol or />-tolyl disulfide in anhydrous carbon tetrachloride.2,3 Benzenesulfenyl chloride has also been obtained by the interaction of hydrogen chloride and N,N-diethylbenzenesulfenamide 4 and by reaction of benzenethiol with N-chlorosuccinimide.6 A comprehensive review dealing with sulfenyl halides and related compounds is available.6... 

The photolyses of diphenyl, di-o-octyl and di-/>-tolyl disulfides in organic solvents at 2540 A produce the corresponding thiols which are formed via H-abstraction of the thiyl radical the quantum yield of thiol formation is 0.046 for all three disulfides . 

Dinitro-di tolyl-disulfide or Dinitro-dimethyl-diphenyl-disulfide, CjjgNgO Sg mw, 336.40, N 8.33%- Several isomers are described in the literature 4,4 -DinilTO-2,2 -ditolyl-disulfide or Bis(4-N ilro-2-me thy l-phenyl)-disulfide, HgC.CgH3(N02)-S.S-(N02).CgHg.CHg,... 

T etrani tro-3,3 -dimethyl-di phenyl-disulfide or Bis(4,6-Dinitro-m-tolyl)-Disulfide,... 

A similar reaction was performed involving 2,2,2-trifluoroethylamine and diphenyl and di-/ -tolyl disulfides. The most suitable conditions were MeCN/Et4NC104/NaBr and utilizing Pt electrodes [55] ... 

The enantiomorphs of a nonplanar disulfide sometimes become separated in crystals. Thus, diphenyl disulfide (43) and probably also di-p-tolyl disulfide (43) crystallize in enantiomorphous space groups with only one enantiomorph per unit cell, and so do barium tetrasulfide monohydrate (1) and sodium tetrathionate dihydrate (101). The same applies, of course, to L-cystine and other optically active disulfides. 

The photochemistry of o/tfto-sulfinyl benzoates has also been investigated [114]. Compound 223 is converted to orf/io-(methylthio)-benzoic acid in 77% yield in benzene. The mechanism of this reaction was not well established, but it probably begins with cleavage of the carbonyl-0 bond, as the same product was obtained from the thioester and selenoester analogs. In these latter cases, tolyl disulfide and tolyl diselenide were also isolated. It was speculated that the 1-photon product of 223 may actually be or//io-(methylsulfinyl)-ben-zaldehyde 161. As discussed in Section V, this compound is known to undergo photochemical intramolecular oxygen transfer. 

---