This research is being funded by the Organic Synthesis Program. This research will study organic compounds which contain carbon atoms that are not directly connected that can still however interact with each other (so-called through-space bonding). Dr. Reingold will use this research project as the vehicle to introduce and to train undergraduate students to chemical techniques in order to stimulate their interests in a career in science. Two projects dealing with such through-space interactions will be studied. The first project will result in the first bishomobenzene derivative, a cyclopropyl-capped semibullvalene, which on rearrangement will also provide the first planar, electronically undisturbed ?8!-annulene. Along the way, new approaches to a variety of related molecules will be developed. The second project will provide a family of compounds which will be the first unambiguous test of the importance of symmetry considerations when pi systems interact through space. Both projects will further our basic understanding of bonding in organic chemistry.
