Alkylsulfanyl group

Alkoxy and alkylsulfanyl groups are also susceptible to aminolysis, although there are few examples of such reactions in the pteridine series. 

The exchange of the alkylsulfanyl group by amino, substituted amino, or hydroxy groups has also been described.109-112,132-137-140-146... 

Exchange of Alkoxy, Aryloxy, and Alkylsulfanyl Groups by Amino Groups... 

The sulfanyl and alkylsulfanyl group has been substituted by alkoxy, amino, hydrazino and hydroxyamino groups85 233 239,242 243 and has also been oxidized to the alkylsulfonyl group which was then replaced by an amino group.233... 

Even more reactive than the alkylsulfanyl group is the alkylsulfonyl group which is replaced by alkoxy and amino groups.161-281-283-290-309 The substitution of an amino group in 6-amino-3-(4-tolyl)-l,2,4-triazin-5(2/f)-one by a thioxo group affords 1 when treated with Lawesson s reagent in dioxane at 100 °C.263... 

Alkylsulfanyl groups are oxidized to yield sulfoxides or sulfones, while thiones are oxidized either to disulfides or sulfonic acids.178,179,18 1 317- 322.347... 

Alkylsulfanyl groups in 1,3,5-triazines are replaced by a chlorine substituent when treated with gaseous chlorine, e.g. as shown in the formation of cyanuric chloride 3. 

The more electron-withdrawing a substituent is the more strongly electrophihc is the carbene. Thus, difluorocarbene is a more electrophilic intermediate than dichlorocarbene. However, if very strong electron-donor substituents such as amino groups, methoxy groups, and alkylsulfanyl groups are present then the carbene may... 

Azepines 3 and (alkylsulfanyl)-dihydroazepines 2 were synthesized by the cyclization of 2-aza-l, 3,5-trienes 1. The proposed mechanism involves deprotonation with base followed by electrocyclic ring closure and either elimination of the alkylsulfanyl group to form the azepine, or reprotonation with water to form the dihydroazepine (14TL2495). 

Alkylsulfanyl groups are stronger donors than alkoxy ones, as shown by the decrease of the oxidation potential from 1.50 V for EDOT to 1.38 and 1.32 V (vs. Ag/AgCl) for EDOST and EDST, respectively [78]. Elowever, this difference is not observed for polymers such as PEDOT, which has a lower oxidation potential and a smaller bandgap than poly(EDST) (Eo = 0.20 vs. 0.90 V and A ,ax = 590 vs. 448 nm) whereas poly(EDOST) represents the intermediate situation [78,79]. This result underlines the major impact of the sulfur atoms of the alkysulfanyl groups on the steric distorsion of the tr-conjugated chain. 

Disulfides and thiolates bind to many transition metals and ligands based on these coordinating groups have been prepared as precursors to electropolymerized films. Electropolymerization of the Pd(II) complex 83 (Chart 5.26), in which the metal is coordinated via alkylsulfanyl groups, was unsuccessful however, partial... 

This result underlines the major impact of the sulfur atoms of the alkylsulfanyl groups on the steric distortion of the jt-conjugated chain [69]. Further work based on crystallographic, electrochemical and spectroscopic analysis of bis-EDOT, bis-EDST and mixed EDOT-EDST dimers has confirmed this fact. Whereas the solid-state structures of bis-EDOT and EDOT-EDST are planar and almost planar, respectively, bis-EDST presents a median torsion angle of 45° [70]. 

To derive the lUPAC name of a sulfide (also called a thioether), select the longest carbon chain as the parent alkane and name the sulfur-containing substituent as an alkylsulfanyl group. To derive a common name, list the groups bonded to sulfur and add the word sulfide to show the presence of the —S— group. 

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