Triethylhexylammonium

Scheme 5.1-20 The reaction between halide and methyl tosylate in triethylhexylammonium...

The first attempt at a nucleophilic substitution reaction in an ionic liquid was carried out by Ford and coworkers [124-126]. Here, the rates of reaction of halide ion (in the form of its triethylammonium salt) with methyl tosylate in the molten salt triethylhexylammonium triethylhexylborate were studied (Scheme 5.2-56). This was compared with similar reactions in dimethyl formamide (DMF) and methanol. The reaction rates in the molten salt appeared to be intermediate in rate between methanol and DMF (a dipolar aprotic solvent known to accelerate Sn2 substitution reactions). 

Scheme 5.2-56 The reaction of halide with methyl tosylate in triethylhexylammonium triethylhexylborate [124-126].

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