Developing Functionalized Peroxide Precursors for the Synthesis of Cyclic and Spirocyclic Ethers

Authors

Anna J. Diepenbrock, University of Nebraska-LincolnFollow

First Advisor

Patrick H. Dussault

Date of this Version

12-2017

Document Type

Article

Citation

Diepenbrock, Anna, "Developing Functionalized Peroxide Precursors for the Synthesis of Cyclic and Spirocyclic Ethers" (2017). Student Research Projects, Dissertations and Theses - Chemistry Department.

Comments

A THESIS Presented to the Faculty of The Graduate College at the University of Nebraska In Partial Fulfillment of Requirements For the Degree of Master of Science, Major: Chemistry, Under the Supervision of Professor Patrick H. Dussault. Lincoln, Nebraska: December, 2017.

Copyright (c) 2017 Anna J. Diepenbrock

Abstract

There is increasing interest in the development of methods for the synthesis of oxetanes and spirocyclic oxetanes, a class of molecules of interest to chemists as they synthesize libraries of possible drug target scaffolds with tunable physiochemical and biological properties.^1,2 Although most ethers are prepared through reaction of nucleophilic oxygen with electrophilic carbon, this work explores new reagents and routes for the synthesis of spirocyclic oxetanes based upon an application of "umpolung" or polarity reversal involving attack of nucleophilic carbon on the electrophilic oxygen of a peroxide (Scheme 1). In this work, a 2-carbon peroxide synthon for reverse etherification has been developed and tested with several nucleophilic substrate.

Advisor: Patrick H. Dussault