RUI: Syntheses, Structures, and Reactions of Strained Cyclic Allenes

Colby College, Waterville ME

Investigators

Abstract

This award from the Chemical Structure, Dynamics and Mechanism Program of the Division of Chemistry supports Professor Dasan M. Thamattoor of the Chemistry Department at Colby College in Waterville, ME in his exploration of the following topics: 1) Generation of strained allene compounds via novel decomposition of spiropentanes; 2) Synthesis of derivatives of 1,2 cycloheptadiene and 1,2 cyclooctadiene that are stable enough to form crystals suitable for x-ray diffraction, and 3) Development of pyrolysis methods for converting cycloalkenylcarbenes to strained cyclic allenes. Computational studies using Density Functional Theory (DFT) would be done in parallel with the experiments to provide insight into product stabilities and reaction pathways. The proposed work, which integrates elements of synthetic, mechanistic, and computational organic chemistry, is designed to provide undergraduates with a wholesome research experience, and enable them to make original contributions to scientific knowledge. Among the most important broader impacts of this research, as mentioned above, is the mentoring of undergraduate researchers and training them as future scientists in a predominantly undergraduate institution. A number of ideas for melding research and education, based on approaches that have already met with success, will be implemented. This is exemplified, for instance, by the incorporation of research-like projects and new pedagogical experiments in the introductory organic chemistry laboratory course. The proposal also seeks to continue Prof. Thamattoor's highly successful program that provides research opportunities to high school students over the summer months. Women, minorities, and students from disadvantaged backgrounds will also be recruited to participate in summer research activities. In addition, there will be new initiative that forges partnerships with elementary school teachers to specifically strengthen the science curriculum in the K-3 level. Finally, it is expected that a number of important fundamental chemical reaction pathways will be elucidated.