creator Sun, Xiang advisor Chong, Hyun-Soon Aziridinium ions are valuable and important intermediates to prepare complex nitrogen containing compounds. Various enantiomerically enriched -haloamines were synthesized as precursors to generate aziridinium ions in situ. Optically active aziridinium perchlorates or triflates were prepared and characterized using 1H and 13C NMR. Regioselective and enantioselective ring opening reactions of aziridinium ions with diverse nucleophilies including cyanide, azide, amines, hydride and water were extensively studied. An efficient one-pot synthetic route to enantiomerically enriched alcohols and amine precursors was developed. Development of the adequate bifunctional chelators is a critical step for radioimmunotherapy (RIT) of cancer. The practical and scalable regiospecific ring opening reactions of aziridinium ions with macrocyclic amines were utilized for synthesis of a series of bifunctional ligands including 3p-C-NETA, C-NE3TA, 3p-C-NE3TA, 3p-C-DECA, 3p-C-DE4TA, an optically active (S)-C-NE3TA, and bifunctional DTPA analogues for RIT using 90Y and 177Lu. Preparation of bifunctional chelators that can rapidly form 64Cu complexes with high stability is an imminent goal for effective PET imaging. A series of NOTA and NE3TA-based chelators were prepared. NE3TA-based bile acid conjugates and NE3TA- based dual receptor-targeted conjugates were synthesized and possess potential for application of targeted PET imaging with 64Cu. Submitted by Liana Khananashvili (khananashvili@iit.edu) on 2014-06-16T19:45:00Z No. of bitstreams: 2 Xiang Thesis final version.pdf: 5754604 bytes, checksum: 20c8132bfd8e9944b9bdef3796d8d4ec (MD5) Signed title page.pdf: 24972 bytes, checksum: 2f88d8c3d81479b6dd6d9128bef1c3d1 (MD5) Made available in DSpace on 2014-06-16T19:45:00Z (GMT). No. of bitstreams: 2 Xiang Thesis final version.pdf: 5754604 bytes, checksum: 20c8132bfd8e9944b9bdef3796d8d4ec (MD5) Signed title page.pdf: 24972 bytes, checksum: 2f88d8c3d81479b6dd6d9128bef1c3d1 (MD5) Previous issue date: 2013-12 PH.D in Chemistry, December 2013 2013 2013-12 http://hdl.handle.net/10560/3268 en Dissertation born digital application/pdf In Copyright http://rightsstatements.org/page/InC/1.0/ Restricted Access CHEM / Chemistry Illinois Institute of Technology Affiliated department