This grant is in the Organic and Macromolecular Chemistry Program. In this study an experimental technique will be employed that will deposit transient molecules at very low temperatures in close proximity to other unstable species so that novel types of reactivity can be discovered and studied. This is an important area of research because it will increase our understanding of how the various electronic properties of highly strained and very reactive organic molecules influence their reactivity and physical characteristics. Professor Staley has judicially chosen his series of model compounds so that they are small enough to be amenable to theoretical study employing high level quantum calculations. Specifically, he will extend his newly developed gas phase vacuum dehydrohalgenation synthetic techniques to the preparation of highly unstable transient molecules at low temperature (-196C) and study their physical properties with a variety of spectroscopic techniques. He will continue his interesting studies of molecules that display Mobius delocalization such as the cycloheptatrienyl anion. His experimental studies will be augmented by advanced level ab initio molecular orbital calculations.