Dibutyl sulfide

CASRN 544-40-1 molecular formula CsHisS FW 146.29 ChemicaPPhysical. MacLeod et al. (1984) studied the reaction of hydroxyl radicals ( limiting reagent ) with dibutyl sulfide in a discharge flow reactor. The rate constants for this reaction at 20,... 

Table 1. Dehydrosulfurization of butanethiol (BuSH) and dibutyl sulfide (Bu2S) at 623 K (the results of second pulses).

Figure 8. The activity of different catalysts in oxidation of n-dibutyl sulfide with hydrogen peroxide.

Dibutyl sulfide is converted into dibutyl sulfoxide with one equivalent of peroxytrifluoroacetic add and into dibutyl sulfone with two equivalents of peroxytrifluoroacetic acid [279]. On the other hand, with manganese dioxide, dibutyl sulfide yields dibutyl sulfoxide exclusively 541], and with chromic acid, it yields dibutyl sulfoxide, even when an excess of the oxidant is used and even when the reaction is carried out at 100 °C 541] (equation 552). 

Trimethylsilyl iodide (TMS-I) can be used as an activating agent in the conversion of sulfoxides to vinyl sulfides providing a sufficiently reactive hindered base, i.e. DIPEA, is employed (Scheme 32). When dibutyl sulfoxide (136) is treated with TMS-I in the presence of HMDS rapid formation of dibutyl sulfide and iodine is observed, indicating that HMDS is too weak a base to effect deprotonation at a rate competitive with iodide ion displacement. Note also that this procedure can be used to prepare 1-thio-phenyl-1,3-butadienes (137) and that either allylic or vinyl sulfoxides can be used as the precursors to these synthetically useful dienes. 

There are also some cases where the support is coated with a homogeneous film that is insoluble in the medium. Dibutyl sulfide was oxidized in methylene chloride to the corresponding sulfoxide quantitatively with cerium ammo-... 

This reaction of sulfides, and also of disulfides, is carried out in the two- to five-fold volume of acetic acid that contains sufficient water to provide the necessary oxygen. Chlorine is led in until the product no longer decolorizes potassium permanganate solution. 1-Butane-sulfonyl chloride is obtained in this way in 80% yield from dibutyl sulfide, and (x-toluene-sulfonyl chloride from dibenzyl sulfide. 

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