PS-thiophenol

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... 

Extension of the isomeric trimellitimide of p-amino benzoic acid with a hydroxy alkyl thiophenol (p-HO-Ph-S-(CH2)n-OH) does yield nematic PEIs (5) [19]. 

It is of interest that the Zn -bound thiophenolate attacks at a methyl carbon atom as electrophilic site, while the Zn -bound alkoxides, as described in Section II, attack at the P atom. In 32, zinc(II) assembles and protects (from oxidation) the four strong nucleophiles CgHgS. While alcohols and water (piiL, both ca. 15) need zinc(II) to be activated at physiological pH, thiophenol (p L, ca. 7) may not require zinc(II) for activation. 

The electrochemical fluorination (Simons cell anhydrous HF electrolyte, sometimes with the addition of NaF to improve conductivity) of benzene, fluoro- and chloro-benzene, w-dichlorobenzene, anisole, o-chloroanisole, thiophenol, p-chloro-thiophenol, iw-thiocresol, 2-chloropyridine, and 3-chloropyridine has been examined in detail (see also p. 212). Benzene and fluorobenzene give mainly dodecafluoro-cyclohexane, but a low yield of chloroundecafluorocyclohexane is obtained from chlorobenzene, and the ethers give fully saturated perfluoroethers with some cleaved products cleavage of the thiophenols leads to extensive formation of SFe. Mixtures of perfluoro-alicyclic and -aliphatic tertiary amines are obtained by similar fluorination of AW-dialkylanilines [PhNEta and PhNMeR (R = Et, Pr, or Bu )] and the three A A -dimethyltoluidines. The relatively new technique (Vol. 2, p. 353) of controlled fluorination at a platinum anode in acetonitrile con-+ -... 

Thiophenol, purchased from Aldrich Chemical Company, Inc., was redistilled before use b.p. 65-66° (42 mm.). 

Benzenesulfonyl chloride, 4-methyl- [p-Tol-uenesulfonyl chloride], 55, 57, 59 Benzenethiol [Phenol, thio-], 55, 122 Benzenethiol, copper(I) salt [Thiophenol, copper(I) salt], 55, 123 Benzenethiol, lithium salt [Thiophenol, lithium salt], 55, 1 22 Benzoic acid, 2-amino- [Anthramlic acid], p bromination of, 55, 23... 

Thiol protection, 59, 190 Thiono esters, reaction with ethyl isocyanoacetate, 59,187 Thionyl chloride, 55, 27 Thiophenol, 55, 122 58, 144 Thorium dodecanedioate, 56,110 Toluene, 56, 86 58,125 p-Toluenesulfonates, reaction with organo-cuprates, 55,112 p-Toluenesulfonic acid, 58, 57, 63 p-Toluenesulfonic acid, monohydrate, 56,44... 

Neilson AH, C Lindgren, P-A Hynning, M Remberger (1988) Methylation of halogenated phenols and thiophenols by cell extracts of Gram-positive and Gram-negative bacteria. Appl Environ Microbiol 54 524-530. 

The hydrothiolation of terminal alkyl alkynes with 96 (Fig. 2.17) proceeds with good degree of regio- and chemo-selectivity, especially with thiophenol and p-methoxy-thiophenol as substrates. Isomerisation to the internal alkenyl thiolates accounts for less than 9% of the thiolated products under the reaction conditions. In addition, further hydrothiolation of the vinyl thioether product is not observed. Typical conversions of 70-85% at 1 mol% loading at 80°C within 5 h are observed. Arylthiols substituted with electron-withdrawing groups afford lower conversions. 

Jones, P.G., Terroba, R., Fernandez, E. and Laguna, M. (2002) Tris (pentafluorophenyl) [2-(diphenylphosphino)thiophenol-kPjgold (III) dichloromethane solvate. Acta Crystallographica, Section E Structure Reports Online, E58(3), m90-m92... 

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) ... 

The base-catalyzed joint reaction of nitroalkenes with thiophenol in the presence of aldehydes gives y-phenylthio-P-nitro alcohols in one pot (Eq. 4.5).8 The joint reaction of nitroalkenes with thiols and a,p-unsaturated nitriles (or esters) has also been achieved. (Eq. 4.6).9 P-Nitro sulfides thus prepared show unique reactivity toward nucleophiles or tin radicals. The nitro... 

Combining, in tandem, the nitro-aldol reaction with the Michael addition using thiophenol is a good method for the preparation of P-nitro sulfides as shown in Eqs. 4.2 and 4.3. This reaction is applied to a total synthesis of tuberine. Tuberine is a simple enamide isolated from Streptomyces amakusaensis and has some structural resemblance to erbastatin, an enamide which has received much attention in recent years as an inhibitor of tyrosine-specific kinases. The reaction of p-anisaldehyde and nitromethane in the presence of thiophenol yields the requisite P-nitro sulfide, which is converted into tuberine via reduction, formylation, oxidation, and thermal elimination of... 

This is a general reaction. It can be used for preparing other selenophenols whenever the desired Grignard reagent can be obtained. The submitter has made the three selenocresols, p-hromophen y 1 scl enophenol, and m-butylselenol by this procedure. He has also obtained thiophenols by the substitution of sulfur for selenium. 

Addition of alcohol occurs on P=N bond of 11,2,3]diazaphospholo[ 1,5-a pyridine (2) and P=C bond of 11,4,2 diazaphospholo[4,5-a Ipyridinc (76) in the presence of sulfur or selenium. In the case of 2, addition is followed by 1,3-H shift and a catalytic amount of the respective alkoxide is required for completion of reaction at room temperature. The reaction of 2 with thiophenol is completed at reflux temperature in the presence of sulfur (Scheme 24) [88],... 

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