Efficient synthesis of a ortho-phenylene-para-phenylene-imine macrocycle

ORGN 451

Thomas S. Hughes, Thomas.S.Hughes@uvm.edu and Andrew L. Korich, Andrew.Korich@uvm.edu. Department of Chemistry, University of Vermont, Cook Physical Sciences Building, 82 University Place, Burlington, VT 05405
Shape-persistent macrocycles are commonly employed as molecular recognition moieties and as building blocks for supramolecular assemblies. Imine linkages have been demonstrated in several cases to be suitable for the construction of such macrocycles, and are usually formed by the reaction of an aldehyde and a separate amine. Herein we report a one-pot reduction and cyclooligomerization of 2-(4-nitrophenyl)-benzaldehyde to give the novel ortho-phenylene-para-phenylene-imine macrocycle 1. Feo and aqueous hydrochloric acid reduce the nitroaldehyde to the AB monomer aminoaldehyde which then undergoes spontaneous macrocyclization to give moderate yields of 1. Because the para-phenylenes can twist out of the plane of the macrocycle, the size of the central cavity of the macrocycle depends on the biaryl torsional angle. The supramolecular behavior of 1 will also be discussed.

 

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005