A modified synthesis, C-functionalization, resolution and racemization kinetics of cross -bridged tetraazamacrocycles

<p>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.</p>

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Dissertation

Year

2009

Author dc:creator

• Odendaal, Antoinette Yolanda

Contributors dc:contributor

• Gary Weisman

• Chemistry
• Organic

Repository record dc:identifier

https://scholars.unh.edu/dissertation/481

OAI identifier oai:identifier

oai:scholars.unh.edu:dissertation-1480