4- Toluenethiol

TOLUENETHIOL see TGPOOO 4-TOLUENETHIOL see TGP250 o-TOLUENETHIOL see TGPOOO p-TOLUENETHIOL see TGP250... 

Toluenethiol. See o-Thiocresol 4-Toluenethiol. See p-Thiocresol a-Toluenethiol. See Benzyl mercaptan o-Toluenethiol. See o-Thiocresol p-Toluenethiol. See p-Thiocresol Toluene trichloride Toluene, a,a,a-trichloro. 

The piefeiied route depends upon the avajlabihty of a hydrogen atom in the beta-position to the thiol group. In other words, a-toluenethiol (in toluene) decomposes to give 1,2-diphenylethane and hydrogen sulfide, via the homolytic route, whereas 2-methyl-2-propanethiol decomposes to give 2-methyl-1-propene and hydrogen sulfide. 

A strong acceptor TCNE undergoes [2+2] rather than [4+2] cycloaddition reactions even with dienes. 1,1-Diphenylbutadiene [20] and 2,5-dimethyl-2,4-hexadiene (Scheme 5) [21] afford mainly and exclusively vinyl cyclobutane derivatives, respectively. In the reactions of 2,5-dimethyl-2,4-hexadiene (1) the observed rate constant, is greater for chloroform solvent than for a more polar solvent, acetonitrile (2) the trapping of a zwitterion intermediate by either methanol or p-toluenethiol was unsuccessful (3) radical initiators such as benzyl peroxide, or radical inhibitors like hydroquinone, have no effect on the rate (4) the entropies of activation are of... 

Solvolysis of either 178a or 178b in 80% aqueous ethanol in the presence of p-toluenethiolate or benzylthiolate gives a 1 1 mixture of cis and trans products. A 1 1 ds trans product ratio also was observed in acetic acid in the presence of either sodium acetate or silver acetate. The 1 1 product ratio was observed as early as 10% reaction and remained constant throughout the reaction. The acetolysis is accompanied by extensive ion-pair return, which causes cis trans, 178a 178b, isomerization. However, this isomerization... 

The anaerobic redaction of dimethyl snlfide to methane (Oremland et al. 1989), and of dibenzyl disulfide to toluenethiol and finally tolnene (Miller 1992) has been described. Methanomethylovorans hollandica is able to grow anaerobically with both dimethyl sulfide and methanethiol (Lomans et al. 1999) whereas dimethyl sulfide, which is used as an electron donor for the growth of Rhodobacter sulfidophilus, is converted into dimethyl sulfoxide (Hanlon et al. 1994). 

The products are (220), probably formed by the dimerization of (219), and the 2-alkoxy-l,2-thiaphosphole derivatives (218). Analogues of the latter are obtained with p-toluenethiol and dialkylamines. The compound (217 R=Ph) is more reactive than (217 R Me ) and will react with aniline on addition of triethylamine even at room temperature, from which the formation of (221) was observed by spectroscopic characterization. Even more reactive is cyclohexylamine which furnishes an analogue of (221) without addition of strong base. ... 

Tioxolone, hl05 TMS, til8 TMSi, t396 Tolan, d742 / -Tolualdehyde, ml38 Toluenethiol, tl42... 

C-Alkylation of weakly activated methylpyridines to yield the isopropyl and tert-butyl derivatives (35-40%), which normally requires the use of strong bases, such alkyl lithiums, is earned out effectively using a phase-transfer catalyst and aqueous sodium hydroxide on the /V-methylpyridinium salts. The pyridines are regenerated by reaction with sodium acetate or sodium 4-toluenethiolate [134]. 3-Methylpyridine fails to react under these conditions and the synthesis of 2-ethylpyridines by this procedure is also unsuccessful. 

Benzothiete sulfone, when treated with LiAlH4 and H30, did not lead to the product corresponding to 232 but rather to o-toluenethiol. ... 

In a different synthesis of 1,5-anhydrohexitols from a compound having a pyranoid ring, Lehmann and Friebolin31 treated 1,5-anhydro-2-deoxy-D-arafemo-hex-l-enitol (D-glucal) (20) with a-toluenethiol in the presence of light, and obtained l,5-anhydro-2-S-benzyl-2-thio-D-mannitol (21) and the epimeric anhydro-D-glucitol in equal amounts. 

TABLE 14. Synthesis of vinyl sulfides (186) by the reaction of magnesium alkyUdene carbenoids with lithium p-toluenethiolate followed by some electrophiles... 

Benzyl mercaptan is another common name for a-toluenethiol. 

Methyl- and 2-aryl-substituted benzo[fc]thiophenes (26) can be synthesized starting from o-toluenethiol in three steps, which involves the intramolecular addition of thiols, produced by acid hydrolysis, to the carbonyl group followed by dehydration as the final step (Scheme 3) (91JHC173). 

There are several examples of this approach to thiophenes. The reaction of thiophenol with acetylene in the vapor phase at 600-650 °C gave benzo[h]thiophene in 71% yield. p-Toluenethiol affords 5-methylbenzo[h ]thiophene in 54% yield under the same conditions (54HC(7)l). The best example of this type of synthesis was the reaction of 3-mercaptocy-clohexanones (235) with glyoxal to form the thiophenes (236), which was the subject of a patent (70USP3511854). The reaction proceeds smoothly under reflux conditions, using ah inert solvent, such as benzene or toluene, which will azeotrope with water, and a protic acid catalyst. A solution of (235) in the solvent is added to 40% aqueous glyoxal solution containing some acid. After reflux the thiophene (236) can be isolated in 70-90% yield. 

Reduction of l,2,4-triazin-3-ones (84) with Raney nickel, zinc and acetic acid, lithium aluminum hydride, sodium borohydride, titanium(III) chloride, p-toluenethiol, hydrogen and a palladium catalyst, or electrochemically, produces 4,5-dihydro-l,2,4-triazin-3-ones (268) (78HC(33)189, p. 246, 80JHC1237), which may be further reduced to 1,4,5,6-tetrahydro-l,2,4-triazin-3-ones (269). l,2,4-Triazin-3-ones (84) with hydriodic acid and phosphorus yielded imidazoles (05LA(339)243). 3-Alkoxy-l,2,4-triazines (126) and sodium borohydride gave the 2,5-dihydro derivatives (270) (80JOC4594). 

The checkers found that the turbidity persisted throughout the addition of the -toluenethiol and that a small amount of an orange-yellow solid was present at the end of the addition. This material dissolved during the concentration under reduced pressure. 

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