Abstract
AbstractThe N‐diazo coupling of p‐chloroaniline with p‐chlorobenzenediazonium tetrafluoroborate in acetonitrile at 30° shows non‐linear base catalysis by water. The results are interpreted in terms of the SE2 mechanism with rate‐limiting proton loss at low base concentration; it is postulated, moreover that the reaction proceeds via transition states in which varying degrees of H‐bonding from the amine and the intermediate ω‐complex to different water species influence the initial step and the base catalysis.
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