Resumen de Rearrangements of Allylic Sulfinates to Sulfones:: A Mechanistic Study
David B. Ball, Paul Mollard, Karl R. Voigtritter, Jenelle Ball
Most current organic chemistry textbooks are organized by functional groups and those of us who teach organic chemistry use functional-group organization in our courses but ask students to learn organic chemistry from a mechanistic approach. To enrich and extend the chemical understanding and knowledge of pericyclic-type reactions for chemistry majors, we introduced into the chemistry-major organic chemistry laboratory a discovery-based, collaborative experiment on the thermal rearrangement of allylic sulfinates to thermodynamically more stable allylic sulfones. The sensitivity of the sulfinate−sulfone rearrangement pathway to substrate structure in this experiment allows the students to investigate the structure−reaction relationship of organic chemistry. Students also encounter the chemical and spectral properties of diasteromers and the necessity of deuterium labeling for product identification.
