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A New Iodination Method
As an unexpected spin-off of the sarain synthesis project, we have discovered a new method for the conversion of alcohols to alkyl iodides. Crystalline salt 10 is readily prepared by reaction of N,N-dimethylthioformamide with methyl iodide. Reaction with a range of primary or secondary alcohols 11 leads, via intermediates 12 and 13, to alkyl iodides 14 in a very clean reaction, with the only by-products being the volatile DMF and methanethiol. We are currently trying to expand this chemistry to incorporate nucleophiles other than iodide.
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