Thioethers arylthio

This reaction is analogous to 10-16. Primary and secondary alcohols can be converted to alkyl aryl sulfides (ROH RSAr) in high yields by treatment with BU3P and an V-(arylthio)succinimide in benzene. Thioethers RSR can be prepared from an alcohol ROH and a halide R Cl by treatment with tetra-methylthiourea Me2NC(=S)NMe2 followed by NaH. ... 

An interesting approach to allenyl thioethers has been reported by Huang and Xiong, which is based on a novel three-component reaction. Treatment of 1-alkynyl-phosphine oxides 310 with lithium alkylthiolates 311 in the presence of an aldehyde 312 provides the expected highly substituted allenyl thioethers 313 in good yield (Scheme 8.84) [173]. Unfortunately, this procedure could not be extended to arylthio-lates. 

Chemoselective oxidation of 3-arylsul-fenylmethyl-A -cephem affords 3-meth-oxymethyl-A -cephem in an anodic substitution. From the two thioethers, the arylthio group is more easily oxididized to a radical cation, that then undergoes cleavage to a thiyl radical and a carbocation (Fig. 31) [152]. 

The effective charge on the sulfur atom in the displacement of an aryl-thio group from an alkyl donor is -0.16 units. The change in effective charge, Ae, is therefore +0.84 from arylthio anion to thioether (Scheme 7). 

Aryl thioethers s. Thioethers, ar. P-(Arylthio)phosphoninm salts... 

Hydrogen chloride N- -C-Arylthio group migration Thioethers from suifenylchlorides... 

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