Allylthiol

Gold nanoparticles can be clearly observed as white dots and silicon wafers are black in HR-SEM images of the gold nanoparticles-immobilized silicon surface. When immobilizing the allylthiol (C3, HS-CHj-CH = CHj)-stabilized gold nanoparticles, even the reaction temperature was as low as 50 °C, the white dots with diameters about lO Onm are observed (Figure 5A). 

Similarly, nitrones react with o.-R -allylthiols to give l,3-thiazolidine-7V-oxides (427). On heating, they are transformed into 1,5,2-oxathiazinanes (428) (Scheme 2.199) (685). 

Tertiary j -nitroso allylthiols 338, heated at 40 °C in benzene or dichloromethane for 6-7 h gave a mrKture of disulfides 339 and nitroso dimers 340 (Equation 51) <2002CC2394>. First formed from 338 is the allyl thiyl radical which isomerizes reversible into the thiiranylcatbinyl radical. Dimerization, after the latter had added to NO, gave 340 and dimerization of the allylthiyl radical gave 339. This topic is also discussed in Section 1.05.6.6. 

Allylthiols and unsaturated lithio sulfones have been found to react as nucleophiles with nitrones to yield intermediate hydroxylamines which undergo reverse-Cope cyclization to provide 1,3-thiazolidine A-oxides and pyrrolidine A-oxides, respectively. In the case of derivatives of C-phenyl nitrone (321 R = Ph), thermolysis was found to result in smooth Meisenheimer rearrangement leading to 1,5,2-oxathiazinane (322) (see Scheme 76). 

Upon treatment of (allylthio)vinylborane 172 with 1 mol% Grubbs catalyst, (GysPizfPhCHiRuCl 173, in methylene chloride, cychzation occurred smoothly to afford a 95% yie of the 2,5-dihydro-l,2-thiaborole 174 as shown in Scheme 17. The precursor 172 is itself readily available ttorn the reaction of allylthiol with diisopropylaminochloro-vmylborane 171 <20000M4935>. Essentially, the same reaction of allyloxyvinylborane 175 with 2% Gmbbs ... 

Deprotonadon of thioanisole and addition of a carbonyl compound affords an isolable hydroxy sulfide which can then be alkylated (Scheme 7). Treatment with base generates the same betaine that would have been formed using the sulfur ylide approach, and effects the intramolecular displacement reaction. The addition of methylthiomethyllithium to 2-cyclohexenone exclusively provides the 1,2-addition prod-uct the dianions derived from phenylmethanethiol or allylthiol react in a similar manner. In one case a 6-keto steroidal substrate was found to undergo smooth methylenation using this procedure. 

Additions to the repertoire of anions stabilized by an adjacent sulphur atom include lithiated polymer-bound methylthiophenyl units which can be used for chain-extension of iodoalkanes, " cyclopropylthiobenzene, and doubly lithiated allylthiol, benzylthiol, and ethyl 2-thioacetate, which all react as C-nucleophiles. 

Synonyms Allyl sulfhydrate Allylthiol 2-Propene-1-thiol Propene-3-thiol... 

Allylthiocarbamide. See Allylthiourea Allyl thiocarbonimide. See Allyl isothiocyanate Allylthiol. See Allyl mercaptan... 

A procedure for selective a- or -y-thioallylation of carbonyl compounds with allylthiol and thioethers has been reported. -Y-Attack occurs with the complex prepared when allylthiol is converted into its bisanion and then reacted with tris(isopropoxy)titanium chloride (Scheme 5, path a). However, the... 

Similar results were observed in the thiophene series . In the rearrangement of allyl 3-thienyl sulphide (105) to 107 and 108, the intermediate 2-allylthiol 106 has been isolated for the first time directly from the reaction mixture. 

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