Di-n-butyl disulfide

Distillation is required to remove the primary side-product, di-n-butyl disulfide. Purification by silica gel chromatography gave inferior results because of similar retention times of the two compounds. The initial distillate fractions are turbid, indicating the presence of di-n-butyl disulfide. The absence of turbidity in the higher boiling fractbn indicates distillate that is predominantly the desired n-butyl 4-chlorophenyl sulfide, containing only small amounts of n-butyl disulfide. 

The reaction mixture is then added to 500 ml. of cold water which has been saturated with sodium chloride. Extraction with ether and distillation gives a little by-product di-n-butyl disulfide and 75 86g. (70-80%) of n-butyl 1-naphthyl sulfide, b.p. 115-I30°/1 mm. 

The yield of HCl was 73% of theoretical. The di-n-butyl disulfide formed was isolated from the reaction mixture by distillation through a column with a yield of 83% of theoretical. By distillation from a Favorskii flask, the residue yielded 14.1 g (75%) of 1,1,7-trichloroheptane contaminated with a small amount of dibutyl disulfide. After redistillation, the 1,1,7-trichloroheptane was obtained in the pure state according to the results of GLC and analysis. 

Figure 11-4. Load-carrying action of organosulfides in the four-ball test. "Extreme-pressure" procedure 60 seconds at 1500 rpm. Additives furnished 1.19% sulfur to the lubricant, a Base oil. 1 Di-n-butyl sulfide. 2 Diphenyl disulfide. 3 Di-n-butyl disulfide. 4 Dibenzyl sulfide. 5 Di-t-butyl disulfide. 6 Dibenzyl disulfide. 7 Diallyl disulfide. From data by E. S. Forbes [32].

Dimethyl sulfoxide oxidizes certain thlo ethers to the sulfoxides in reasonable yield. The ether is heated with a 50% molar excess of DMSO at 160-175° for several hours and the dimethyl sulfide is removed by distillation as formed. The suifoxides were isolated in high purity by distillation and there was no evidence of sulfone formation. Di-n-butyl sulfoxide and tetraethylene sulfoxide were obtained in similar yield, but several sulfides did not react to an appreciable extent. DMSO is a superior reagent for the oxidation of thiols to disulfides. A solution of the thiol in NHj MHj... 

The N tert butanesulfinyl chiral auxiliary 32 has become the reagent of choice for the preparation of a branched amines due to its excellent level of diastereocontrol and the fact that the steric hindrance caused by the tert butyl group aids in the minimization of side reactions [32d]. The preparation of this chiral auxiliary in enantiomerically pure form is easily achieved in two steps and 65% overall yield starting from di tert butyl disulfide (Scheme 1.15) [55]. The nucleophilic addition of... 

Measurements have been made by Koch (152, 153) on disulfides and diethyl, diphenyl, and di-2-benzthiazyl tetrasulfide and dicyclohexyl hexasulfide, and by the following authors on complete series R2S with n = 1 through 4 Baer and Carmack (12) for R = n-hexadecyl, Minoura for R = benzyl (176) and p-tolyl (177), and Haszeldine and Kidd (142) for R = trifluoromethyl. Harris (140) has recorded the spectra of the di-o-nitrophenyl mono- through pentasulfide series, Gorin and Dougherty (135) those of the di-n-alkyl disulfides from methyl through butyl, and dimethyl... 

For the sulfenylation of the less strongly basic ketone-enolates the more reactive thiosulfonates R"SS02R", thiocyanates R"SC=N or sulfenyl halides R"SC1 (or Br), may be used instead of dialkyl disulfides. In many cases, however, the reaction with the more easily obtainable disulfides is sufficiently fast. Di-tcrt-butyl disulfide, t-BuSS-f-Bu reacts very sluggishly, even with the most strongly basic organometallics. 

Naftocit MBT. See 2-Mercaptobenzothiazole Naftocit MBTS. See Benzothiazyl disulfide Naftocit Mi 12-C. See Ethylene thiourea Naftocit NaDBC. See Sodium di-n-butyl dithiocarbamate Naftocit Na DEC. See Sodium diethyidithiocarbamate Naftocit NaDMC. See Sodium dimethyidithiocarbamate Naftocit Thiuram 16. See Tetramethylthiuram disulfide... 

Weedone LV4, see 2,4-D Weedone MCPA ester, see MCPA Weedrhap, see 2,4-D, MCPA Weed tox, see 2,4-D Weedtrine-D, see Diquat Weedtrol, see 2,4-D Weeviltox, see Carbon disulfide Wham EZ, see Propanil Winterwash, see 4,6-Diiutro-o-cresol Witicizer 300, see Di-n-butyl phthalate Witophen P, see Pentachlorophenol WL 18236, see Methomyl WL 19805, see Cyanazine WL 43467, see Cypermethrin WL 43479, see Permethrin WL 43775, see Fenvalerate WN 12, see Methylisothiocyanate Wonuk, see Atrazine Wotexit, see Trichlorfon X-all liquid, see Amitrole... 

An irradiated soln. of di- er -butyl disulfide in methanol containing methylene blue as sensitizer treated with oxygen until uptake stops after 3.5 hrs. tert-butyl er -butanethiolsulfinate. Y 15%. F. e. s. R.W. Murray and S. L. Jindal, J. Org. Chem. 37, 3516 (1972) review of thiolsulfinic acid esters s. N. Isenberg and M. Grdinic, Intern. J. Sulfur Chem. 8, 307 (1973). 

Di-n-butyl Sulfide (CH3CH2CH2CH2)2S or dibutyl disulfide (CH3CH2CH2CH2S)2-... 

Alkyl disulfides, trialkyl phosphites, and CO react to give good yields of thio-esters via a radical chain.—E n-Butyl disulfide heated 11-16 hrs. at 120-144° with triethyl phosphite and di-ferf-butyl peroxide under 325 atm. GO-pressure in a glass-lined autoclave n-butyl pentanethiolate. Y almost 100%.—High yields are favored either by high CO-pressure or low disulfide concentration. F. new reactions s. C. Walling, O. H. Basedow, and E. S. Savas, Am. Soc. 82, 2181 (1960). 

Bis(t-butyl) phenol. See 2,6-Di-t-butylphenol Bis (n-butyl) sebacate. See Dibutyl sebacate Bis-butyl xanthogen. See Dibutyl xanthogen disulfide... 

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