Allen Julia Margaret author Columbia University. Chemistry Lambert Tristan H. thesis advisor Columbia University. Chemistry Columbia University. Chemistry originator text Dissertations 2011 English The first synthesis and full characterization of a new functionality, called the diaziridinium ion, is reported. The original synthetic intent behind its design was to explore its potential use as a non-metal based N-transfer reagent. During this study, we have uncovered a practical rearrangement to access 2,3-benzodiazepines reliably and efficiently. Efforts to achieve N-transfer from these species are described and are ongoing. We have identified the tropylium ion as a highly efficient organic-based amine oxidant and have demonstrated its practical use in a one-pot protocol for alpha-aminonitrile synthesis. We also report an application of this new oxidant towards an aza-Cope rearrangement. Finally, we report a multicatalytic method that uses bismuth(III) triflate to catalyze a nucleophilic addition to an aldehyde followed by hydroalkoxylation to generate highly functionalized tetrahydrofuran rings, a motif that is often encountered in natural product architectures. Ph.D., Columbia University. Organic chemistry http://hdl.handle.net/10022/AC:P:10595 NNC NNC 2011-06-27 15:48:04 -0400 2011-06-27 15:53:59 -0400 4545 eng