Author

Hong Yin

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.

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