Organic oxidants, including quinones, oxoammonium ions, and trityl cations, abstract hydride ions to form carbocations. This review describes the mechanistic foundations for these processes and the vast array of their applications in synthesis.
Re 2 O 7 in hexafluoroisopropyl alcohol provides access to cationic intermediates from alcohols through the intermediacy of perrhenate esters. This manuscript describes the application of the system to the formation of a number of weakly basic heterocyclic systems through dehydration reactions and intramolecular nucleophilic addition. The influence of the substrate structure on the reaction rates and stereocontrol is discussed with respect to intermediate ion pairs.
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