Synthesis and chemistry of 1,3,5-triazinyl diazenes: Direct reduction of diazene linkages to hydrazo groups with hydrazine

ORGN 760

William Koppes, koppeswm@ih.navy.mil1, David M. Rosenberg, RosenbergDM@ih.navy.mil2, Brian W. Vos1, Jimmie C. Oxley, joxley@chm.uri.edu3, and Jesse S. Moran, jmoran@chm.uri.edu3. (1) Indian Head Division, Naval Surface Warfare Center, Indian Head, MD 20640, (2) Research and Technology, Indian Head Division, Naval Surface Warfare Center, 101 Strauss Ave, Indian Head, MD 20640, (3) Dept of Chemistry, University of Rhode Island, Kingston, RI 02881
Linear, cyclic, and dendritic oligomers of 1,3,5-triazines with hydrazo and diazene linkages are of interest as scaffolds for the synthesis of energetic materials. The synthesis of prototype low molecular weight compounds with methoxy substituents will be described, as well as their analogs with NH2- , Cl-, NH2NH-, and other substituents. In the course of this work we observed that the azo linkages could be reduced with hydrazine to form hydrazo linkages while producing another mole of reducing agent, presumed to be the diimide byproduct of the hydrazine oxidation. The scope of this reaction was determined with other azo substrates.

 

Heterocycles and Aromatics
1:00 PM-5:00 PM, Thursday, 1 September 2005 Washington DC Convention Center -- Ballroom B, Oral

Division of Organic Chemistry

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