Date of Award

Fall 2007

Project Type


Program or Major


Degree Name

Master of Science

First Advisor

Edward H Wong


This thesis presents the synthesis of a novel tricyclic bisamidine, 3,2,3-BisAm 9 (2,3,4,6,7,9,10,11-octahydro-pyrazino[1,2-a:4,3-a'] dipyrimidine) and its coordination chemistry with transition metals. By comparison with its analogue 2,2,2-BisAm, which has diverse coordination modes including both symmetrical and unsymmetrical chelating as well as metal-bridging coordination modes, 3,2,3-BisAm, with a substantially larger ideal bite angle, only exhibits the chelating mode. The preparation and characterization of its complexes with W(0), Cu(II), Pd(II), Zn(II), Cd(II), Hg(II), Ag(I), and Eu(III) will be discussed in detail.

This thesis also describes the completion of a novel multi-step synthesis from S-valine of a C2 symmetric chiral 2,2,2-BisAm 71 (2,9-diisopropyl-2,3,5,6,8,9-hexa hydro-diimidazo [1,2-a;2',1'-c] pyrazine, which can potentially serve as a chiral ligand in asymmetric catalysis. In addition, the synthesis of a C 2 symmetric chiral 3,2,3-BisAm 74 was initiated by adopting the same synthetic strategy. On the basis of these studies, a general synthetic route can be developed to prepare C2-symmetric tricyclic bisamidines from chiral amino acids.*.