Chemical Dynamics and Green Chemistry Strategies with Solid-to-Solid Reactions

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With this renewal award, the Organic and Macromolecular Chemistry Program continues its support of the work of Professor Miguel A. Garcia-Garibay, of the Chemistry Department at the University of California-Los Angeles. This research will investigate solid-state photochemical reactions and green chemistry strategies with solid-to-solid reactions. A series of mechanistic studies with several crystalline cyclohexanone derivatives possessing radical-stabilizing substituents will be carried out. These compounds, which can undergo a clean decarbonylation reaction, will provide a reliable entry to the preparation of radical pairs and biradicals in crystals. With the synthesis of prostaglandins in mind, studies designed to address the photochemical reactivity of unsaturated carbonyl compounds will be undertaken. Factors that affect the quantum yield and selectivity of these solid-state photochemical reactions will be evaluated. Additional studies that probe the chemical behavior of biradicals and singlet carbenes in crystals will be carried out. The role of quantum mechanical tunneling in solid-state reactions will also be investigated.Graduate, undergraduate and post-doctoral students involved in this research will receive interdisciplinary training in techniques and methods that range from synthetic organic and solid-state chemistry to materials science. This research project will continue successful efforts to attract female and minority students to a highly supportive and creative environment. The impact of this work extends beyond UCLA through research collaborations with several neighboring institutions with no Ph.D. programs. The results of the proposed research will contribute to the solution of important problems in solid-state and green chemistry.