Walking on water: Which alcohols react with nucleophiles on the surface of water? The correlations introduced by Mayr et al., in which electrophiles are characterized by the parameter E, gives practical indications about the reactivity of alcohols with nucleophiles in pure water. Stable carbocations generated from the alcohols and characterized by E<−2.5 readily react with nucleophiles in pure water at 80 °C, without added Brønsted or Lewis acids.
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Cozzi et al. (2008) studied this question.
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