Dimethylsulfoxide dialkylation

Zinc dialkyls do not react with phenylacetylene in Et20 but do so in more strongly polar aprotic solvents. The reaction half-lives decrease with increasing donor power of solvent, e.g., in reaction (b) with t/2 values of 270 in N,N-dimethylformamide (DMF), 200 in dimethylsulfoxide (DMSO) and < 8 s in hexamethylphosphoramide (HMPA). ... 

If the crown catalyzed reaction of potassium superoxide with alkyl halide is carried out in dimethylsulfoxide as solvent, the product is the corresponding alcohol [6—9]. The formation of alcohol rather than dialkyl peroxide has been shown to result from reaction of the alkyl hydroperoxide anion with dimethylsulfoxide to form alkoxide and dimethylsulfone (Eqs. 8.3-8.5) [9]. The alkyl hydroperoxide anion is presumably formed by reduction of the initial alkyl hydroperoxide radical by the superoxide anion [8, 9]. 

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