Our synthetic research efforts are focused on the preparation and computational analysis of small ring compounds with aromatic-induced charge separation. A current target compound is 5-(cycloprop-2-en-1-ylidene)cyclopenta-1,3-diene, more commonly known as Calicene, which is a fulvalene that exhibits two cross-conjugated rings connected through a common exocyclic double bond. The extent of the molecular dipole calculated for Calicene, and assorted heterocyclic analogs, is directly proportional to the extent of aromatic stabilization of the cross-conjugated ring systems.
Other research efforts include the development and introduction of an optical activity laboratory experiment for the sophomore organic instructional laboratories. This novel experiment involves the standard NaBH4 and Luche reductions of (-)-Menthone in alcoholic solvents to yield varying ratios of diastereomeric (-)-Menthol and (+)-Neomenthol. These ratios, which vary depending on the alcoholic solvent, can be determined by comparing the observed optical rotation for the product mixture to the standard optical rotations of pure (-)-Menthol and (+)-Neomenthol. Further studies exploring solvent-mediated diastereoselectivity are currently underway.
A third area of research involves the use of classroom response systems (clickers) to study decision pathways employed by students in problem-solving. The elucidation of organic reactions and pathways often involves a series of decision points, much like branches in logic decision trees. Each alternative at a decision point is associated with a unique letter or number which may, for example, represent a synthetic reagent or a locant on a parent chain. Students respond to in-lecture example problems by entering into their clickers a series of alphanumeric characters which describes the decision pathway they followed to solve the problem. We are currently developing a databank of these series response questions that will provide insight into the problem solving strategies utilized by students.