This grant in the Organic and Macromolecular Chemistry Program supports research by Prof. David Reingold, which is aimed at elucidating features of electronic interactions between atoms in a molecule which are not bonded to each other. Organic chemists believe they have a sound understanding of electron sharing between bonded carbon atoms. However, recent advances in the synthesis of strained-ring organic molecules demonstrate gaps in our understanding of the concepts of bonding and electron-sharing. This work is aimed at synthesizing and exploring the chemistry of molecules which have significant electron density between non-bonded atoms. Two different projects are planned. In the first, Dr. Reingold plans to prepare a family of compounds which should provide a test of the Goldstein-Hoffmann theory of through-space (longicyclic) conjugation. In the second, Dr. Reingold will synthesize what could be the first bishomobenzene derivative, a cyclopropasemibullvalene. On rearrangement, this should provide the first planar, electronically unperturbed ?8!annulene.
