Abstract by Dakota Jones
Chemistry and Biochemistry
Iminyl Radical Cyclizations of Oxime Ethers
Radical reactions are an enticing way of synthesizing new organic compounds, as they do not require expensive or toxic catalysts and are selective as to the bonds that they form. Over the last year, I have investigated the radical reactions of the oxime ether C17H14NO, derived from phenoxyamine and phenyl 3-butenyl ketone, with a variety of radical traps, including TEMPO, acrylate, and halomethanes. Other radical traps are also known, and I am currently working on a radical reaction of the same oxime ether with Togni’s reagent, which attaches a –CF3 group. For the radical traps tested so far, a reaction temperature of 120°C for 120 minutes has given the best results. Yields have been variable but usually between 20-60%, with TEMPO and CCl4 giving the best yields. Moving forward, it is hoped that the radical reactions will be achieved with diastereoselectivity due to a chair-like transition state.