A complex, tricyclic compound is synthesized in two steps from simple starting materials. Infrared, 1H NMR and 13C NMR spectroscopy allow for the determination of the product’s structures, with two-dimensional 1H–1H correlation spectroscopy (COSY) being the most important spectroscopic tool for determining the structure of the final product. The novel mechanism for the formation of the final product is also discussed. This investigation is suitable for upper-level organic chemistry students.
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Peter S. Marrs (2007) studied this question.
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