Centennial Honors College
Western Illinois University
Undergraduate Research Day 2012
Poster Presentation
Oxidative Cleavage of Alkenes Using an In-Situ Generated Iodonium Ion: A pH
Dependent Investigation
Amanda Ellison
Faculty Mentor: T. K. Vinod
Chemistry
Oxidative cleavage of alkenes is a synthetically important transformation emphasized
during the first term of a sophomore undergraduate organic chemistry curriculum. The
practical difficulties with the ozonolysis procedure make it an inconvenient experiment
for undergraduate students to carry out. We have recently described a facile and
operationally convenient catalytic procedure for oxidative cleavage of alkenes. In situ
formed [hydroxy(4-carboxyphenyl)iodonium]ion, from the oxidation of 4-iodobenzoic
acid, has been shown to facilitate the cleavage of a variety of alkenes in presence of
Oxone as a co-oxidant. Optimization of this convenient procedure using 1-phenyl-1cyclohexene as a protypical substrate to develop a useful undergraduate experiment at
different pHs will be described.