Scope and mechanism of the Huisgen zwitterion condensation reaction

The Huisgen zwitterion is a useful reagent as its prevalent use in the Mitsunobu reaction shows. A novel condensation reaction of the zwitterion of a phosphine and azodicarboxylate species has been shown. Work has been done expanding upon the current scope of this condensation reaction to include beta-hydroxyketones. A variety of beta-hydroxyketones and other compounds have been reacted with the Huisgen zwitterion, formed from diisopropylazodicarboxylate (DIAD) and triphenylphosphine, yielding hydrazone carbamates as the condensation products. A mechanism of this condensation reaction is proposed based on the scope of the reaction as examined in this thesis.