Benzylmercaptan reaction with

Benzylmercaptan reacts with diacetylenes 57 under base-catalyzed conditions in aregio- and stereoselective fashion to form diadducts Z,Z-l,4-di(benzylthio)buta-1,3-dienes (59). In this case, monoadducts 58 can be isolated (96T12677). The reaction with r-butylmercaptans gives good results for diacetylenes with aromatic substituents. 

It was found that much better yields are obtained if the vinylpyridine is first converted into the corresponding benzyl pyridylethyl sulfide (by reaction with benzylmercaptan), followed by pyrolysis of the latter over glass helices at high temperature with either nitrogen or hydrogen sulfide as carrier gas37 I Eq. (16)]. 

Transesterification (thiol exchange by reaction of a dithioe-ster with a thiol). Thioglycolic acid-based dithioesters are poor RAFT agents. FFowever, they can serve as precursors to other RAFT agents as they undergo facile reaction with other thiols to provide new dithioesters. For example, reaction of dithioester 86 with benzylmercaptan provides benzyl dithiobenzoate (103) in high yield (Scheme 25). ... 

The Sucholeiki thioether linkage can be synthesized via a disulfide bond (NpSSMpact) and addition of benzylbromide 408 or alternatively via the chlorine derivative and following reaction with benzylmercaptan. Other syntheses start from thiols that are converted with electrophiles. 

Reaction between benzylmercaptans and haloacetic acids yield benzylmercaptoacetic acids (57) which, via their acid chlorides, undergo an intramolecular Friedel-Crafts cyclization to produce isothiochromanones as in Eq. (24).233-235 Attempts to cyclize 57 with sulfuric acid,... 

Fig. 8. Recording of t—E curves during the course of a reaction Reaction of S-ben-zyl-isothiuronium chloride with hydroxide and carbonate ions in carbonate buffer pH 9.7. Initial concentration of S-benzylisothiuronium chloride 4 x 10 4M. Anodic waves of benzylmercaptan formed were recorded after intervals given in the polarogram. Curves starting at — 1.0 V towards more positive potentials, S.C. E., 200 mV/absc., h = 70 cm, full scale sensitivity 2.2 p.A...

An account has also been given of the reaction between benzylmercaptan and cis-benzene trioxide.With a-mercapto esters, p-substituted phenyloxiranes undergo normal opening, without being affected by the substituents on the benzene ring. Chalcone oxides react with mercaptan with accompanying C-C bond cleavage (Eq. 308). ... 

Cyanide addition to the lactamic carbonyl group has been described in a reaction in which the cyanide ion acts as a catalyst (Fig. 14).The intermediate acyl cyanide can be attacked by an added nucleophile (allylic, propargylic, benzylic alcohols, aniline, benzylmercaptan). Comparative experiments were carried out using more classical procedures, such as under catalysis by potassium cyanide with stirring at room temperature, and with sodium alkoxides at -78 C. This last method provides the highest yields, up to 95% in most of the cases tested, but the sonochemical method proceeds under less basic conditions. Both methods preserve the integrity of the asymmetric center. 

For example, Meerwein Reaction of 78 followed by displacement of the resultant chloride with the sodium salt of benzylmercaptan provides 79. Conversion of the ester to the amide followed by oxidative chlorination/amination yields the sulfonamide 81. 

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