One-step conversion of alcohols into nitriles with simultaneous two-carbon chain elongation. (Cyanomethyl)trimethylphosphonium iodide as a reagent with a dual mode of action

Treatment of alcohols with an excess of (cyanomethyl)trimethylphosphonium iodide leads, after aqueous hydrolysis, to the clean formation of nitriles with two more carbon atoms than present in the original alcohol. Benzylic, allylic, and aliphatic alcohols without beta-branching (RCH(2)CH(2)OH) have been converted to nitriles with success. The required phosphonium iodide is simple to prepare and can be stored for a long time at room temperature.