The Transfer of Nucleophiles into Organic Solvents

Displacement by cyanide works particularly well, and many other nucleophilic substitution reactions are enhanced by PTC. Most monovalent anions can be transferred, including alkoxides, phenoxides, thiocyanates, nitrates, nitrites, superoxides and all of the hahdes. Divalent anions are usually too hydrophilic to be transferred into the organic phase. 

Typically, the organic substrate in these reactions is a haloalkane. Primary haloalkanes will generally give 100% substitution products, but tertiary and cyclohexyl halides usually undergo 100% elimination, with secondary haloalkanes producing a mixture of the two. Studies of the chloride and bromide displacements of (/ )-2-octyl methanesulfonate have shown that phase transfer displacements proceed with almost complete inversion of stereochemistry at the carbon centre, indicating an Sjv2-like mechanistic pathway [41]. 

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