Dibenzyl sulfide, derivative

Examination of Table I reveals that the edge of dibenzothiophene is displaced from that of dibenzyl sulfide, the first inflection energy being some 0.6 eV higher for the former compound. From previous XANES data on dibenzothiophene and dibenzyl sulfide and physical mixtures of the two, it proved possible to identify each compound in the presence of the other (3b,8). Additionally by simply measuring the heights of the third derivative features at 2469.8 eV and 2470.4 eV relative to the base line in the model compound mixtures, a calibration was established which allowed an approximate estimate of the amounts of each component in hydrocarbon samples to be obtained. 

Figure 2. Sulfur XANES spectra of mixed dibenzothiophene and dibenzyl sulfide. The left panel shows the absorption spectra, and the right panel the corresponding third derivatives, from top to bottom, pure dibenzothiophene, a 1 1 molar mixture of dibenzothiophene and dibenzylsulfide, and pure dibenzylsulfide...

Figure 3. Calibration plot for quantification of dibenzothiophene and dibenzyl sulfide mixtures, from mixtures of the pure compounds. Points denoted as "A" indicate the third derivative amplitude at 2469.8 eV, and those as "0" the third derivative amplitude at 2470.4 eV.

Benzotrichlorides have also been prepared via another sulfur derivative. Dibenzyl sulfides (RC6H4CH2)2S with R= o,m,p-Me, 0-Br,/ -NO2 are chlorinated in CC14 at 80 °C to give 27-91% of RC6H4CC13882 883. 

Procedure Dibenzyl sulfide (50 mg) is dissolved in 1 ml of glacial acetic acid and mixed with 0.2 ml of 10% hydrogen peroxide. The mixture is heated and boiled gently for 3 min. The hot solution is diluted with water until it becomes turbid, the turbidity is dissolved by heating, and eventually the solution is allowed to cool slowly. The precipitated derivative is filtered off under suction and washed twice with 0.5 ml of water. Yield 48 mg, mp 134 °C, which drops after crystallization from 2 ml of 50% ethanol to 27 mg, mp 134 °C. 

Few examples of photooxidation of selenides are known. Hiotolysis of dilute aerated solutions of dibenzyl diselenide in benzene resulted in the formation of benzaldehyde and elemental selenium. i Without oxygen present during the photolysis only decomposition to dibenzyl selenide and selenium was observed. i 1 Photolysis in CDCb in an NMR tube in the presence of oxygen gave complex mixtures of products derived fnm benzyl radicals. It appears that monoselenides are more stable dian die corresponding sulfides and teUurides to phouxixidadon. ... 

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