Date of Degree

9-2020

Document Type

Dissertation

Degree Name

Ph.D.

Program

Chemistry

Advisor

Shengping Zheng

Committee Members

Ryan Murelli

Yu Chen

Subject Categories

Organic Chemistry

Keywords

Chlorination, Fluorination, Synthesis

Abstract

Organic compounds containing halogen are an important and useful class of intermediates that can be converted to other functionalities. This thesis describes our strategy in selective chlorination and fluorination of quinols to offer the corresponding aromatic structures. Quinols, or cyclohexadienones, as oxidized derivatives of phenols, have their remarkable chemical reactivities, including additions to enone, enolate alkylations, aldol reactions, cycloadditions, and rearrangements. Dienone-phenol rearrangement provides the asymmetric route since the stereocenters located in the six-membered ring of various cyclohexadienone were widely using in building larger chiral arrays for many total syntheses

Chapter one of this thesis discusses our new selective nucleophilic chlorination of quinol to afford ortho- chloride phenol. This one-step selective chlorination can easily be performed using readily available quinols and thionyl chloride. In Chapter two, inspired by chlorination strategy, we develop a new fluorination strategy to offer fluorinated cyclohexadienone products by deoxofluorination of quinols. Chapter three describes our study work on the total synthesis of Strongylophorine-26. The difficulties we met and our solution is discussed.

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