Date of Award

Spring 2009

Project Type


Program or Major


Degree Name

Doctor of Philosophy

First Advisor

Gary Weisman


Modifications to the literature-reported procedure for the synthesis of cross-bridged cyclam and homocyclen tetraamines are presented. The synthesis involves the use of a cis-tricyclic bisaminal intermediate for the preparation of tetracyclic bisaminals and the microwave-assisted reductive ring opening of N,N'-dibenzyl bisaminal salts. The cis-tricyclic bisaminal was also used in the preparation of a C-functionalized cross-bridged cyclam. The resolution of racemic cross-bridged cyclam by selective crystallization of its diastereomeric salt of L-(+)-tartaric acid is described. Additionally, the kinetics of racemization of enantiopure cross-bridged cyclam is presented.