Semester
Summer
Date of Graduation
2008
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Abstract
Cyclobutenediones have proven useful as starting materials for synthesis of highly functionalized biologically relevant molecules. The rearrangement of cyclobutendiones has a wide synthetic scope and can be utilized as a key step in the construction of quinones, benzo[o]isoxazoles, and 3-methylenoxoindoles having a variety of substitution patterns. Construction of these molecules involves thermolysis of 4-hydroxy-2,4-di-aryl-2-cyclobutenones derived from squaric acid ester. In each of the cases the mechanism proceeds through an initial ring opening of the cyclobutene to afford a ketene intermediate that subsequently undergoes a ring closure with various intermolecular nucleophiles. This methodology has been utilized in the construction of an ellipticine model system.
Recommended Citation
Fisher, Kimberly Denise, "Thermal rearrangement of 4-aryl-4-hydroxy-2-cyclobuten-1-ones and application of the methodology in the formation of benzofuronaphthoquinones and benzocarbazolequinones" (2008). Graduate Theses, Dissertations, and Problem Reports (ETD). 4372.
https://researchrepository.wvu.edu/etd/4372