Chemistry, Department of


Date of this Version



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, 2012

Copyright (c) 2012 Benjamin W. Puffer


A common reaction to yield ethers relies on an alkoxide nucleophile and a carbon electrophile (Williamson ether formation). Ethers can also be formed by reactions with carbon nucleophiles and oxygen electrophiles by way of the peroxide functional group. We screened a number of carbon nucleophiles suitable for attack on dialkyl peroxides to form new C-O bonds. Also a novel approach using a peroxyketal electrophile is shown to increase the efficiency of this intermolecular reaction. This method of C-O bond formation can also be implemented intramolecularly, not seen before in the literature, to yield cyclic ethers. This approach requires the generation of an organolithium, via lithium/heteroatom exchange, in the presence of a peroxide. The intramolecular C-O bond formation is shown here to yield 5 and 6-membered ethers as well as oxetenes.

Advisor: Patrick H. Dussault