In our upper division integrated laboratory sequence, we have introduced experiments that require chemistry majors to investigate the versatility and limitations of modern spectroscopic techniques. Such an experiment is the determination of the conformational preference of the conformationally mobile 2-bromo-3,3,5,5-tetramethylcyclohexanone in solvents of varying dielectric constant using IR, 1H NMR, UV and computational analyses. This determination require conformationally static model compounds of comparable structure and electronic distribution to the alpha-bromotetramethylcyclohexanone. Exo- and endo-2-bromobicyclo[3.2.1]octan-3-one is a model system that allows students to determine the conformational preferences in the mobile bromoketone. The classical synthesis of the bicycloketone precursor involves a relatively poor three step conversions (carbene addition, allylic halide removal, and acidic hydrolysis if a vinyl halide). Herein, we have developed a higher yielding synthetic sequence utilizing a [4 + 3] cycloaddition. Included in this project is a computational study of this cycloaddition process.

Synthesis and computational analysis of a conformationally static model system

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