RUI: Synthetic and Mechanistic Studies of Quinone-Organozinc Alkylation Reactions

Lebanon Valley College, Annville PA

Investigators

Abstract

The focus of this research involves the development of methodology for use of organozinc reagents as selective quinone alkylating agents. Mechanistic studies will stress regiochemistry, chemoselectivity and the presence or absence of free radical intermediates. The reagents will be used to synthesize mono- and dialkylated naphthoquinones, pyranoquinone derivatives and alpha-substituted quinone derivatives of esters. Undergraduate co-workers will form an important part of the research effort. With this Research in Undergraduate Institutions (RUI) award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Carl T. Wigal in the Department of Chemistry at Lebanon Valley College. Professor Wigal will focus his research efforts on developing methodology for the use of organozinc reagents for the preparation of polysubstituted quinones that will serve as precursors for the synthesis of complex molecules having biological significance. There is potential for broader impact of the work for the pharmaceutical industry and the project presents an excellent arena for the training of undergraduate students.