Rearrangements of Allylic Sulfinates to Sulfones:: A Mechanistic Study

• David B. Ball ^[1] ; Paul Mollard ^[1] ; Karl R. Voigtritter ^[1] ; Jenelle L. Ball ^[1]
  1. [1] California State University, California
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 87, Nº 7 (July), 2010, págs. 717-720
• Idioma: inglés
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• Resumen

  • 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.