Redox efficiency: Exploring the role of hydride shifts in organic chemistry

Lead Research Organisation: University of Oxford
Department Name: Oxford Chemistry


Chemistry, and the ability to make molecules, is a central subject that is at the heart of many different scientific endeavours. Organic chemistry is especially concerned with the reactivity of carbon in all of its different forms and can be viewed as a study of the chemistry taking place within living things. Organic chemists are constantly looking for new ways of designing and building new molecules (synthetic chemistry is essentially molecular architecture) with interesting and exciting properties. Novel organic molecules lie at the centre of the pharmaceutical industry and they can be designed to have useful biological activity and eventually for use as medicines.

The key aspect of our proposed research is a new route to carbocyclic molecules by using a rearrangement of hydrogen atoms within a molecule (known here as a hydride shift). This particular reaction allows us to control the placement of functionality with a complex molecule with great efficiency such that carbocyclic compounds, such as cyclohexenes and benzenes, can be made with great precision; and in this case the reaction uses key promoters to make reactions run in ways that are not possible without them. The complex and cyclic molecules generated by this new approach are found in many different compounds of value in both the academic and commercial world, and application of this new method will lead to both new science and new applications of organic molecules. Moreover, the development of powerful and efficient new chemical reactions has beneficial consequences for the environmental impact of the chemical processes involved (ie new reactivity with increased efficiency and reduced waste).

The novel chemistry proposed herein will lead to a new, efficient and powerful way of making cyclic compounds to control all aspects of the structures of the products formed: this will be of great benefit to both academia and industry who will be able to make interesting and useful molecules in new ways. We have engaged a project partner from the pharmaceutical industry so that the project will develop rapidly into areas that are of direct interest and value to industry.

The real advantage of this proposal is the development of cutting edge science and its application to solve problems that are relevant to chemical scientists around the world.


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