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Synthesis 1994; 1994(3): 276-278
DOI: 10.1055/s-1994-25458
short paper
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Superelectrophilic Methylthiomethylation of Aromatics with Chloromethyl Methyl Sulfide/Aluminum Chloride (MeSCH2Cl:2AlCl3) Reagent

George A. Olah* , Qi Wang, Gebhard Neyer
  • *Donald P. and Katherine B. Loker Hydrocarbon Chemistry Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA
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Publication Date:
27 September 2002 (online)

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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.