Semester
Summer
Date of Graduation
2014
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Bjorn C. Soderberg
Committee Co-Chair
Patrick S. Callery
Committee Member
John H. Penn
Committee Member
Alan M. Stolzenberg
Committee Member
Kung K. Wang
Abstract
We have discovered a practical general method for the preparation of diverse 2-halomethylene-4-cyclopentene-1,3-diones and/or 2-halo-1,4-benzoquinones. An in-depth study of the reactions of 4-(ethynyl)-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones with N-bromo- or N-iodosuccinimide is described. This reaction was used in a short total synthesis of methyl linderone. Also, a series of facile, palladium catalyzed, direct, and regiospecific Wacker-type oxidations has been developed to yield various alpha-arylated ketones from aryl-substituted internal alkenes.
Recommended Citation
Yin, Hong, "Formation of 2-halomethylene-4-cyclopentene-1,3-diones and/or 2-halo-1,4-benzoquinones, total synthesis of methyl linderone and Wacker-type oxidation of aryl-substituted alkenes" (2014). Graduate Theses, Dissertations, and Problem Reports. 389.
https://researchrepository.wvu.edu/etd/389