I. Selective Chlorination and Fluorination of Quinols II. Synthetic Study of Strongylophorine-26

<p>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</p> <p>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.</p>

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Chemistry

Grantor

The Graduate School and University Center of The City University of New York

Year dc:date.available

2020

Author dc:creator

• Li, Sihan

Advisor dc:contributor.advisor

• Shengping Zheng

Committee members dc:contributor.committeemember

• Ryan Murelli
• Yu Chen

• Organic Chemistry
• Chlorination
• Fluorination
• Synthesis

Repository record dc:identifier

https://academicworks.cuny.edu/gc_etds/4018

OAI identifier oai:identifier

oai:academicworks.cuny.edu:gc_etds-5080