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.
","abstract_html":"<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>","abstract_has_math":false,"creators":["Li, Sihan"],"institution":"The Graduate School and University Center of The City University of New York","degree_name":"Doctor of Philosophy","degree_level":"Doctoral","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":["Shengping Zheng"],"committee_chairs":[],"committee_members":["Ryan Murelli","Yu Chen"],"year":2020,"date_issued":"2020-09-01T07:00:00Z","date_published":"2020-09-01T07:00:00Z","updated_at":"2026-07-24T01:58:22Z","subjects":["Organic Chemistry","Chlorination","Fluorination","Synthesis"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://academicworks.cuny.edu/gc_etds/4018","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Shengping Zheng"]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["Ryan Murelli","Yu Chen"]},{"key":"dc:creator","label":"Author","values":["Li, Sihan"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2020-09-04T07:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Doctoral"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["The Graduate School and University Center of The City University of New York"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Organic Chemistry","Chlorination","Fluorination","Synthesis"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://academicworks.cuny.edu/gc_etds/4018"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:title","label":"Title","values":["I. Selective Chlorination and Fluorination of Quinols II. Synthetic Study of Strongylophorine-26"]}]}],"canonical_facts":{"dc:contributor.advisor":["Shengping Zheng"],"dc:contributor.committeemember":["Ryan Murelli","Yu Chen"],"dc:creator":["Li, Sihan"],"dc:date.available":["2020-09-04T07:00:00Z"],"dc:description.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.
"],"dc:identifier":["https://academicworks.cuny.edu/gc_etds/4018"],"dc:subject":["Organic Chemistry","Chlorination","Fluorination","Synthesis"],"dc:title":["I. Selective Chlorination and Fluorination of Quinols II. Synthetic Study of Strongylophorine-26"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Doctoral"],"thesis:degree_name":["Doctor of Philosophy"],"thesis:institution_name":["The Graduate School and University Center of The City University of New York"]},"updated_at":"2026-07-24T01:58:22Z"}