Abstract by Siyeon (Sia) Im
Siyeon (Sia) Im
Chemistry and Biochemistry
Fragmentation of oxime ether rings
By subjecting a cyclic oxime ether to microwave irradiation, fragmentation of the oxime ether ring can be induced in order to to generate a cyanide and a primary radical. Radical traps such as TEMPO and isopropyl iodide can be used in the iminyl radical fragmentation, installing oxygen- and iodine-containing functional groups. Oxygen, carbon, and nitrogen donating radicals are used to create C-C bonds, C-O bonds, and C-N bonds. Methanol, trifluoro-toluene, and acetonitrile each give 80% or higher yields of the nitrile product. Acetonitrile yields the highest percent yield (94%) due to its polarity. Thus, we will use acetonitrile for our primary solvent. Various radical traps and different oxime ethers will continue to be explored in our further studies of this fragmentation.