Quaternary benzylammonium ion rearrangements with organolithium compounds—I: Simple tertiary amines from the attack of N-butyl-lithium on benzyltrimethylammonium iodide

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Benzyltrimethylammonium (I) iodide reacts with n-butyllithium to produce α,N,N-trimethylbenzylamine (II) and o,N,N-trimethylbenzylamine (III) in a monomeric rearrangement process. A 51% total yield of the two simple tertiary amines contained II and III in the ratio of 1:3·8. Separation of the reaction products by gas chromatography and identification by IR and PMR indicated the absence of other rearrangement products [i.e. N-benzyl-N-ethylmethylamine (IV) and β-phenethyldimethylamine (V)] from the methyl ylide of I. The failure of V to be consumed in the presence of n-butyllithium eliminated secondary reactions as the feature limiting the number of observed products. The products II and III have previously been reported separately in other rearrangements of I.