Part I. Aromatic Fluorinations for Fluorine-18 Labeling of Estrogens. Part Ii. Bromodesilylation-Potential Method for Regiospecific Radiobromination of Aromatic Systems. Part Iii. Synthesis of Isohexestrol and Isohexestrol Derivatives

Two aromatic fluorination methods, the decomposition of aryl azides and the decomposition of aryl triazenes, were investigated as methods potentially suitable for fluorine-18 labeling of estrogens. The aryl triazene method gives moderate yields in many systems, but fails with ortho methoxy or methanesulfonyloxy groups. The aryl azide method gives good yields of p-fluoroanilines, which can be deaminated readily, but oxygen or large alkyl groups ortho to the azide interfere with the fluorination. The synthesis of meta-fluorohexestrol, a non-steroidal estrogen with high binding affinity for the estrogen receptor, was achieved via the aryl triazene decomposition method. This method was also extended to aromatic bromination in the synthesis of meta-bromohexestrol.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Ng, Johny Sau-Hoi

• Chemistry, Organic

Identifier

(UMI)AAI8203542

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70165