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

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.

Name thesis:degree_name

PhD

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Year dc:date.available

2014

Author dc:creator

• Yin, Hong

Contributors dc:contributor

• Bjorn C. Soderberg
• Patrick S. Callery
• John H. Penn
• Alan M. Stolzenberg
• Kung K. Wang

• Organic chemistry

Identifier

https://researchrepository.wvu.edu/etd/389

OAI identifier oai:identifier

oai:researchrepository.wvu.edu:etd-1392