The base-catalysed rearrangement of the allylpropynyl ammonium cations (I) in aqueous solution yields either the isomeric cations (II) or the aldehydes (III) and (IV), or mixtures of (II), (III), and (IV); this result contrasts dramatically with the transformations of (I) observed in aprotic solvents.
T. Laird and W. D. Ollis, J. Chem. Soc., Chem. Commun., 1972, 557 DOI: 10.1039/C39720000557
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