N-Butyl methyl sulfide

A soln. of (n-butylthio)acetic acid irradiated 2.67 hrs. with Pyrex-filtered light of a 100 w. medium-pressure Hg-lamp in benzene containing benzophenone as sensitizer and thiophenol -> n-butyl methyl sulfide. Y ca. 100% based on startg. m. consumed. F. e. and sensitizers s. R. S. Davidson and P. R. Steiner, Soc. (C) 1971, 1682, 3480 without sensitizer cf. R. S. Goudie and P. N. Preston, Soc. (C) 1971, 3081. 

Ethyl vinyl sulfide Isopropyl methyl sulfide Methyl n-propyl sulfide leri-Butyl methyl sulfide Chloromethyl methyl sulfide Ethyl isopropyl sulfide Isobutyl methyl sulfide Methyl 2-methylallyl sulfide Allyl ethyl sulfide Ethyl n-propyl sulfide... 

Komori and Nonaka132,133 electrochemically oxidized methyl, isopropyl, n-butyl, isobutyl, r-butyl and cyclohexyl phenyl sulfides (108) and cyclohexyl p-tolyl sulfide (109) to their sulfoxides using a variety of polyamino acid-coated electrodes to obtain the range of e.e. values shown in parentheses. The highest enantiomeric purities were obtained using an electrode doubly coated with polypyrrole and poly(L-valine), an electrode which also proved the most durable of those prepared. 

NONANOL n-NONYL MERCAPTAN BUTYL-PENTYL-SULFIDE ETHYL-HEPTYL-SULFIDE HEXYL-PROPYL-SULFIDE METHYL-OCTYL-SULFIDE n-NONYLAMINE... 

HEPTANOL 5-HETHYL-l-HEXANOL ISOPROPYL-TERT-BUTYL-ETHER n-HEPTYL MERCAPTAN BUTYL-PROPYL-SULFIDE ETHYL-PENTYL-SULFIDE HEXYL-METHYL-SULFIDE... 

Compound Name Polypropylene Glycol Tetrahydrofuran Dimethyl Sulfide N-Butyl Mercaptan Thiophosgene Ammonium Thiocyanate Ethyl Mercaptan Methyl Mercaptan Thiophosgene Phosphorus Pentasulfide Thiram Thiram... 

The submitters used N-chlorosuccinimidc, 4-tert-butyl-cyclohexanol, methyl sulfide, and triethylamine, available from Aldrich Chemical Company, Inc., without further purification. 

Commercial polymers have been produced from methyl, ethyl, isopropyl, n-butyl, isotubtyl, t-butyl, stcaryl, benzyl and trimethylsilyl vinyl ethers. The polylmethyl vinyl ether) called PVM or Resyn is produced by the polymerization of the monomer by boron trifluoride in propane at —40°C in the presence of traces of an alkyl phenyl sulfide. The polymer may have isotactic, syndiotactic or stereoblock configurations depending on the solvent and catalyst used. 

Table 6C. 1 lists representative results for the asymmetric oxidation of thio ethers with r-butyl hydroperoxide under the standard conditions (in dichloromethane at -20°C). Enantioselectivi-ties are especially good (80-95% ee) for the oxidation of aryl methyl sufoxides (Table 6C.1). A substantial decrease in enantioselectivity is observed for oxidation of aryl-S-alkyl-type sulfides in which an alkyl group is larger than methyl such as n-propyl an n-butyl.

Moreover, the formation of enoxy-silanes via silylation of ketones127 by means of N-methyl-N-TMS-acetamide (1 72) in presence of sodium trimethylsilanolate (173) was reported in 1969 and since then, the use of silylating reagents in presence of a catalyst has found wide appreciation and growing utilization as shown in recent papers128-132 (Scheme 27). Diacetyl (181) can be converted by trifluoromethylsul-fonic acid-TMS-ester (182) into 2,3-bis(trimethylsiloxy)-l, 3-butadiene (7treatment with ethyl TMS acetate (7 5)/tetrakis(n-butyl)amine fluoride l-trimethylsiloxy-2-methyl-styrene (i<56)130. Cyclohexanone reacts with the combination dimethyl-TMS-amine (18 7)/p-toluenesulfonic acid to 1-trimethylsiloxy-l-cyclohexene (iSS)131. Similarly, acetylacetone plus phenyl-triethylsilyl-sulfide (189) afford 2-triethylsiloxy-2-pentene-4-one (790)132. ... 

Model reactions showed that 2-dodecyl-5-methyl thiophene, benzo[b]thiophene, 2-n-butyl benzo[b]thiophene and dibenzothiophene were unaffected by these reaction conditions after a 4-hour reflux. For the LiAlH4 reduction step the solvent dioxane (b.p. 100°C) is preferred to either diethyl ether or tetrahydrofuran since preferential reduction of certain sulfides in the latter solvents has been observed (2). The results of the sulfide analyses for several petroleums from Alberta are summarized in Table I. 

PB PBI PBMA PBO PBT(H) PBTP PC PCHMA PCTFE PDAP PDMS PE PEHD PELD PEMD PEC PEEK PEG PEI PEK PEN PEO PES PET PF PI PIB PMA PMMA PMI PMP POB POM PP PPE PPP PPPE PPQ PPS PPSU PS PSU PTFE PTMT PU PUR Poly(n.butylene) Poly(benzimidazole) Poly(n.butyl methacrylate) Poly(benzoxazole) Poly(benzthiazole) Poly(butylene glycol terephthalate) Polycarbonate Poly(cyclohexyl methacrylate) Poly(chloro-trifluoro ethylene) Poly(diallyl phthalate) Poly(dimethyl siloxane) Polyethylene High density polyethylene Low density polyethylene Medium density polyethylene Chlorinated polyethylene Poly-ether-ether ketone poly(ethylene glycol) Poly-ether-imide Poly-ether ketone Poly(ethylene-2,6-naphthalene dicarboxylate) Poly(ethylene oxide) Poly-ether sulfone Poly(ethylene terephthalate) Phenol formaldehyde resin Polyimide Polyisobutylene Poly(methyl acrylate) Poly(methyl methacrylate) Poly(methacryl imide) Poly(methylpentene) Poly(hydroxy-benzoate) Polyoxymethylene = polyacetal = polyformaldehyde Polypropylene Poly (2,6-dimethyl-l,4-phenylene ether) = Poly(phenylene oxide) Polyp araphenylene Poly(2,6-diphenyl-l,4-phenylene ether) Poly(phenyl quinoxaline) Polyphenylene sulfide, polysulfide Polyphenylene sulfone Polystyrene Polysulfone Poly(tetrafluoroethylene) Poly(tetramethylene terephthalate) Polyurethane Polyurethane rubber... 

Commercially available solutions of H3B-THF in THF (Aldrich-Boranes, Inc., 2371 N. 30th St., Milwaukee, WI 53210) which are used in this synthesis, contain approximately 5% of sodium tetrahydroboratefl —) as a stabilizer. Tri(sec-butyl)borane prepared from these solutions should be distilled. An alternative commercial (Aldrich-Boranes, Inc.) hydroborating agent free of sodium tetrahydroborate(l —) is borane-methyl sulfide. 

MACROLiDEs Chloiomethyl methyl sulfide. Dialkylhoryl trifluori imethanesulfonate. Di-n-hutyltin oxide. Dichloroketene. 4-Di-methylamino-3-butyi e-2-one. Keteny 1 i-dene triphenylphospl orane. Tetra-n-butyl-ammonium fluoride. 1,1,6,6-Tetra-n-butyI-1,6-distanna-2,5,7, lO-tetraoxycyclodecane. Tetrakisftriphenylphdsphine)-palladium. N,N,N,Nl-Tetramethylchloro-formamidinium chloride. 

AMINO GROUP Boron trifluoride ether-ale. l-r-Bulyloxycarbonyltriazole-1,2,4, Di-t-butyl dicarbonate. 4-Dimethylamino-1-t-butyloxycarbonyl pyridinium chloride. CARBONYL GROUP Ceric ammonium nitrate. 1,2-Dihydroxy-3-bromopropane. Sodium N-chloro-p-toluenesulfonamide. Thallium(lll) nitrate. Trichloroethanol. Trimcthylsilyl cyanide. Chloromethyl methyl sulfide. N,N -Diisopropylhydra-zinc. Trichloroethanol. 

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