Subphthalocyanines from a new method of synthesizing ortho-aromatic nitriles

ORGN 619

Peter Schuchmann, Max-Planck-Institut fur Bioanorganische Chemie, Mulheim, Germany, C. Michael McCallum, mmccallum@pacific.edu, Department of Chemistry, University of the Pacific, 3601 Pacific Ave., Stockton, CA 95211, and Ronald Nohr, nohrrs@saclink.csus.edu, Department of Chemistry, Sacramento State University, Sacramento, CA 95819.
Subphthalocyanines are boron–containing aromatic macrocycles synthesized from ortho-aromatic nitriles. The synthetic availability of unsubstituted and substituted 1,2- phenyl, naphthyl, and anthryl nitriles is limited for the formation of the cyclized three diiminoindoline units N-fused around a boron atom. A new synthetic method to readily produce ortho-aromatic nitriles from dibromides and dichlorides will be presented. Mechanistic schemes will be discussed with supporting Hammett correlation diagrams and quantum mechanical calculations in order to characterize reactant-to-product transition states along with bond energy considerations.
 

Physical Organic Chemistry: Calculations, Mechanisms, Photochemistry, and High-Energy Species
8:00 AM-12:00 PM, Thursday, 30 March 2006 Georgia World Congress Center -- C303, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006