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Effective methylthiomethylation of aromatics was achieved by using chloromethyl methyl sulfide/aluminum chloride (MeSCH2Cl:2AICl3) as the alkylating agent. Excess aluminum chloride activates the thiocarboxonium ion intermediate by coordinating with sulfur and thus diminishes back donation of "electron density" into the carbocationic center, rendering it a superelectrophilic methylthiomethylating agent.
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Olah et al. (1994) studied this question.
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