The Ohio State University. Department of Chemistry Honors Theses; 2007
This thesis describes a new synthetic pathway for the preparation of molecular basket 1. Earlier synthetic difficulties comprising harsh experimental conditions (high pressure) and low diastereoselectivities were resolved in herein described procedures. That is, molecular basket 1 is now obtained in a diastereoselective Cu (II) promoted cyclotrimerization of stannylated norborene 7 (syn/ anti =1:1.4) in a good yield (41%). The folding of 1 was examined with 1H NMR spectroscopy. An incremental addition of Cu (I) to its solution caused considerable changes in its 1H NMR spectrum and ascribed to the folding of its pyridine arms about the Cu (I) cation.