Dissertations, Theses, and Capstone Projects
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.
Recommended Citation
Li, Sihan, "I. Selective Chlorination and Fluorination of Quinols II. Synthetic Study of Strongylophorine-26" (2020). CUNY Academic Works.
https://academicworks.cuny.edu/gc_etds/4018