RUI: Strained Cycloalkynes

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In this project funded by the Chemical Structure, Dynamic & Mechanism B Program of the Chemistry Division, Professor Dasan Thamattoor of the Department of Chemistry at Colby College is developing new approaches to small-ring compounds containing a triple bond. As the triple bond prefers a linear geometry, incorporating this feature inside a small ring can lead to considerable strain. Investigating such strained molecules can teach us about structure, bonding, energetics, and chemical reactivity. It can lead to the design of new reactions for the preparations of pharmaceuticals and energetic materials. The project, which integrates elements of synthetic, mechanistic, and computational organic chemistry, is designed to provide undergraduates with a wholesome research experience, and engage them as partners in the scientific enterprise. In addition, several initiatives to promote the delivery of high quality education in Science, Technology, Engineering, and Mathematics (STEM) in the local schools (K-12) will be pursued. This includes providing summer research opportunities for high school students and partnering with educators in the elementary, middle, and junior high schools to enhance STEM offerings. The project contains a set of aims, appropriate for an undergraduate-driven research program, to generate strained cycloalkynes from new photochemical and thermal sources. These sources are based on cyclopropanated phenanthrene and indan systems and are to be studied for the generation of known and new carbocyclic, heterocyclic, and polycyclic alkynes. Matrix isolation and time-resolved laser flash photolysis will be used to study the kinetics of the cyclic alkylidenecarbene intermediates. Flash vacuum pyrolysis will be studied as a complementary approach to the photochemical route for generating these strained cycloalkynes. The chemistry of strained cycloalkynes, with respect to the pathways by which they are formed and consumed, will also be investigated by modern computational methods.