Chemistry, Department of


Date of this Version



Benjamin Enns. Synthesis and Applications of Cyclobutenes. MS. Thesis, University of Nebraska-Lincoln, Lincoln, NE, 2016.


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: April, 2016

Copyright © 2016 Benjamin D. Enns


Our group is interested in cyclobutene analogs of fatty acids as reactive coatings, potential antibiotics, and as a new class of bioconjugate linkers. A convenient synthesis of this class of molecules was previously reported from our lab. However, ammonia, a key reagent in the earlier route, was recently reclassified as a highly corrosive gas requiring highly specialized equipment for storage and handling. The goal of this research was to find a convenient synthesis for the formation of cyclobutene that did not involve the use of ammonia. The other part of this thesis describes the preparation of a short chain cyclobutene fatty acid as a substrate for conjugation to an amino acid as part of a collaboration targeting the synthesis of proteins, which could be selectively modified using the cyclobutene/tetrazine "click" reaction.

Advisor: Patrick H. Dussault