The ambident nucleophilicity of sulphenate anions
Abstract
2-Nitro-4-trifluoromethylbenzene- and 2-nitrobenzene-sulphenate anions, generated by the base-catalysed hydrolysis of the corresponding disulphide or sulphenate ester, undergo S-methylation with methyl iodide but predominantly O-methylation with the ‘harder’ methylating agents, methyl fluorosulphonate and dimethyl sulphate. Sulphinate ions react similarly with methyl fluorosulphonate.