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By the addition of small amounts of a phosphonium salt such as hexadecyltributylphosphonium bromide, cyanide ions can be ferried from the water phase into an organic phase (e.g., bromooctane + some hydrocarbon). With the phase transfer catalyst, nonanenitrile (1-cyanooctane) forms quantitatively in 90 minutes at reflux.[1]
C8H17Br(org) + NaCN(aq) > C8H17CN(org) + NaBr(aq) (catalyzed by a R4P+Cl? PTC)
Subsequent work by Herriott and Picker[2] demonstrated that many such reactions can be performed rapidly at around room temperature by using catalysts such as tetra-n-butylammonium bromide or methyltrioctylammonium chloride in benzene/water systems...
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