Reactions of sulfone-substituted ketenes

CHED 431

Jordan Hill, jordanhill123@yahoo.com, Jenna Wilson, wils0863@benedictine.edu, Linda Myers, lmyers2005@yahoo.com, Natalie Russo, russ0943@benedictine.edu, Jacob Schesser, sb173ahk@carsoncomm.com, and Aileen T. Beard. Department of Chemistry & Biochemistry, Benedictine College, 1020 N. 2nd, Atchison, KS 66002
We have been investigating the versatility of sulfone substituted ketenes (e.g. 1) in [2+2] cycladdition reactions. The cyclic products of these reactions have much potential for use in the synthesis of biologically active molecules. We have previously reported a novel preparation of sulfone ketenes from a sulfone-substituted acid chloride. In a single pot, the sulfone-substituted carboxylic acid can be converted to the acid chloride, followed by treatment with base and subsequent trapping of the resultant sulfone ketene. This presentation will examine the products of several of these cycloaddition reactions, utilizing a variety of unsaturated compounds as trapping agents.