Identification of the products of solvolysis of N-benzylpyridinium cations in the absence of nucleophiles
Abstract
Mono-, tri-, and penta-cyclic N-benzylpyridinium tetrafluoroborates undergo thermolysis in chlorobenzene as solvent to give products of benzylation both of the solvent and of the pyridine leaving group. Thermolysis alone, and in nitrobenzene as solvent, yielded mainly products of benzylation of the leaving group. The results support the previously postulated mechanism of unimolecular solvolysis of compounds of these types in non-polar solvents.
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