P-Tolyl mercaptan

Thio-p-cresol (p-tolyl mercaptan), p-CHjCjH SH. This compound may be similarly prepared from p-toluenesulphonyl chloride (Section IV,207). The thio-p-cresol crystallises in the steam distillate and is collected and dried m.p. 43°. The b.p. under normal pressure is 194r-195°. 

SYNS p-MERCAPTOTOLUENE p-METHYLBEN-ZENETHIOL 4-METHYLBENZENETHIOL p-METH-YLPHENYLMERCAPTAN 4-METHYLPHENYLMER-CAPTAN p-METHYLTHIOPHENOL 4-METHYL-THIOPHENOL p-THIOCRESOL 4-THIOCRESOL 4-TOLUENETHIOL p-TOLYL MERCAPTAN D p-TOL-YLTHIOL USAF EK-510... 

TOLYL ISOCYANATE see IKG725 o-TOLYL ISOCYANATE see IKG725 o-TOLYL MERCAPTAN see TGPOOO p-TOLYL MERCAPTAN see TGP250 a-TOLYL MERCAPTAN see TGO750... 

Synonyms 4-Mercaptotoluene p-Mercaptotoluene 4-Methylbenzenethiol p-Methylbenzenethiol 4-Methylphenyl mercaptan p-Methylphenyl mercaptan 4-Methylthiophenol p-Methylthiophenol 4-Thiocresol 4-Toluenethiol p-Toluenethiol 4-Tolyl mercaptan p-Tolyl mercaptan p-Tolylthiol Classification Aromatic mercaptan Empiricai CyHaS Formuia CH3C6H4SH... 

Tolyl mercaptan. See p-Thiocresol a-Tolyl mercaptan. See Benzyl mercaptan o-Tolyl mercaptan. See o-Thiocresol p-Tolyl mercaptan. See p-Thiocresol p-Tolyl 3-methyl butyrate. See p-Cresyl isovalerate... 

Allyl p-tolyl sulphoxide 535 reacts with sodium methoxide in methanol by initial prototropic isomerization and subsequent addition of methanol to give 536 (equation 333). Protic solvents are photochemically incorporated by the open chain olefinic bond of trans methyl )S-styryl sulphoxide 537 in a Markovnikov regiospecificity (equation 334). Mercaptanes and thiophenols add to vinyl sulphoxides in a similar manner (compare also Reference 604 and Section IV.B.3) to give fi-alkylthio(arylthio)ethyl sulphoxides 538 (equation 335). Addition of deuteriated thio-phenol (PhSD) to optically active p-tolyl vinyl sulphoxide is accompanied by a low asymmetric a-induction not exceeding 10% (equation 336) . Addition of amines to vinyl sulphoxides proceeds in the same way giving )S-aminoethyl sulphoxides in good to quantitative yields depending on the substituents at the vinyl moiety When optically active p-tolyl vinyl sulphoxides are used in this reaction, diastereoisomeric mixtures are always formed and asymmetric induction at the p- and a-carbon atoms is 80 20 (R = H, R = Me) and 1.8 1 (R = Me, R = H), respectively (equation 337) ... 

Amines react in general more readily than alcohols and aromatic isocyanides are more reactive than ahphatic ones. The ionic diisocyanide complexes react under milder conditions than the neutral monoisocyanide complexes . No reactions with mercaptanes have been reported. Acyclic aminocarbene complexes occur as isomers when R R due to restricted rotation around the C(carbene)—N bond . Dinuclear carbene complexes are formed when the amine complexes [Au(C6F5)NH2(CH2)nNH2] (n = 1 or 2) or the carbene complexes [(C6F5) ,AuC(NHR)NH(CH2)nNH2] (m = 1 or 3) are treated with the isocyanide compound [(C6F5)mAuCNR] (R = Ph or p-tolyl) . ... 

Tetramethylpyrazlne Theaspirane 2-Thienyl mercaptan Thymol Tolualdehyde glyceryl acetal, mixed o, m, p p-Tolylacetaldehyde Tolyl aldehyde p-Tolyl aldehyde 4-(p-Tolyl)-2-butanone o-Tolyl isobutyrate... 

A stirred soln. of N-p-tolylmaleimide and benzene in CSg heated on a water bath and treated gradually with AICI3, heating continued 6 hrs. 3-phenyl-N-p-tolyl uccinimide. Y 85%. F. e., also addition of mercaptans and amines to the carbon-carbon double bond, s. A. Mustafa et al., J. Org. Chem. 26, 787 (1961). 

The best evidence for the photolytic decomposition of mercaptans and disulfides into free radicals involves photoinitiation of polymerization of olefins. Thus, photolysis of disulfides initiates the copolymerization of butadiene and styrene,154 as well as the polymerization of styrene207 and of acrylonitrile.19 Thiophenol and other thiols promote polymerization upon ultraviolet irradiation.19 Furthermore, the exchange of RS-groups between disulfides and thiols is greatly accelerated by light. Representative examples are benzothiazolyl disulfide and 2-mercapto-thiazole,90 tolyl disulfide and p-thiocresol, and benzyl disulfide and benzylmercaptan.91 The reaction probably has a free radical mechanism. Similar exchange reactions have been observed of RS-groups of pairs of disulfides have been observed.19... 

Solution-polymerized SBR is made by termination-free, anionic/live polymerization initiated by alkyl lithium compounds. Other lithium compounds are suitable (such as aryl, alkaryl, aralkyl, tolyl, xylyl lithium, and ot/p-naphtyl lithium as well as their blends), but alkyl lithium compounds are the most commonly used in industry. The absence of a spontaneous termination step enables the synthesis of polymers possessing a very narrow molecular weight distribution and less branching. Carbon dioxide, water, oxygen, ethanol, mercaptans, and primary/secondary amines interfere with the activity of alkyl lithium catalysts, so the polymerization must be carried out in clean, near-anhydrous conditions. Stirred bed or agitated stainless steel reactors are widely used commercially. 

---