4-methoxyphenyl dimethyl sulfoxide

Methoxyphenyl Tellurium Cyanide8 0.47 g (1.0 mmol) of bis[4-methoxyphenyl] ditellurium, 0.19 g (3.0 mmol) of potassium cyanide, and 10 ml of dimethyl sulfoxide are placed in a conical flask, The mixture is stirred for 3 h at 20°, diluted with water, extracted with diethyl ether, and the extract is diluted with hexane. The resultant organic solution is washed thoroughly with water, dried with anhydrous sodium sulfate,... 

With the exception of a few examples of nucleophilic attack on the thiocarbonyl group, including a more recently published method using sodium hydroxide under phase transfer conditions,most conversions are carried out with oxidative reagents. Sodium peroxide, dimethyl sulfoxide with acid or iodine,selenium-derived reagents and bis(p-methoxyphenyl)telluroxide have been used. 

The second example is the telomerization of phthalic acid with butadiene yielding bis(octadienyl) phthalates, which can then be hydrogenated to the bisoctyl phthalates which may be used as plastic softeners. The catalyst is formed from palladium bis(acetylacetonate) and tris(p-methoxyphenyl)phosphite in the polar solvent dimethyl sulfoxide. Once again the extraction can be carried out with isooctane [58, 59]. 

Triethylamine added at 60° to Na previously dispersed at 110° under dry Ng in xylene containing a little oleic acid, then phenylacetylene in xylene added drop-wise at a rate to keep the temp, at ca. 60°, after the exothermic reaction has ceased warmed 0.5 hr. at the same temp., bis-(p-methoxyphenyl)carbodiimide in xylene added dropwise at room temp, during 10 min., finally dimethyl sulfoxide in xylene added with water-cooling, and the product isolated after 0.5 hr. -> N,N -bis-(p-methoxyphenyl)phenylpropiolamidine. Y 65%. - No significant reaction occurs in the absence of dimethyl sulfoxide. F. e., also with ethylmagnesium bromide instead of Na, s. H. Fujita et al.. Bull. Chem. Soc. Japan 45, 1846 (1972). 

Oxidation of star polymethylene 6 affords 3 equiv. of a-hydroxy-co-(4-methoxyphenyl) polymethylene 5 with DP = n. The strict correspondence between stoichiometry and DP in these examples is consistent with a rapid initiation and the absence of termination or chain transfer reactions in the polymerization of ylide 1. The absence of a termination step is reasonable, since the living end of this polymer is a trialkylborane, which is stable under the reaction conditions. Dimethyl sulfoxide (DMSO), a byproduct that accumulates during the reaction does not inhibit the initiator/catalyst. 

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