O and S methylation of the ambident p-toluenesulfinate anion

The alkylation of the p-toluenesulfinate anion in methanol or dimethylformamide by methyl iodide, methyl sulfate, and methyl p-toluenesulfonate gives both methyl p-toluenesulfinate and methyl p-tolyl sulfone. Alkylation of the ambident anion with hard alkylating agents gives predominantly the ester, whereas a soft alkylating agent gives predominantly the sulfone.