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About: Nonclassical ion     Goto   Sponge   NotDistinct   Permalink

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Nonclassical carbocations are stabilized by charge delocalization from contributions of neighbouring C−C or C−H bonds, which can form bridged intermediates or transition states. Nonclassical ions have been extensively studied with the 2-norbornyl system, which as “naked” ion unambiguously exhibit such a bridged structure. The landmark of nonclassical ions are unexpectedly fast solvolysis rates and large differences between epimeric esters. Such behaviour is not restricted to 2-norbornyl esters, as has been shown with some cyclopentyl and steroidal esters with the tosyloxy leaving group.