Synthesis of O-alkylarylhydroximoyl azides

ORGN 481

Artie S. McKim, amckim@gaylordchem.com, Gaylord Chemical Corporation, 209 Industrial Parkway, Bogalusa, LA 70427 and Debra D. Dolliver, ddolliver@selu.edu, Department of Chemistry & Physics, Southeastern Louisiana University, SLU 10878, Hammond, LA 70402.
We report the first general synthesis for O-alkylarylhydroximoyl azides. This synthesis produces a single geometric isomer. These organoazides offer potential routes to heterocyclic systems containing oxime ether substituents of specific stereochemistry. A series of these compounds with ring substituents varying from electron-donating to electron-withdrawing were produced. The stability of these compounds and their reactivity in Schmidt-type rearrangements and 1,3-dipolar addition reactions will be discussed.