The Two Faces of Sulfinates: Illustrating Umpolung Reactivity

• Adabelia Tapia-Pineda ^[1] ; Carlos Perez-Arrieta ^[1] ; Carolina Silva-Cuevas ^[1] ; Ehecatl Paleo ^[1] ; J. Armando Lujan-Montelongo ^[1]
  1. [1] Instituto Politécnico Nacional

     Instituto Politécnico Nacional

     México

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 93, Nº 8, 2016, págs. 1470-1474
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • A simple, microscale experiment was developed with the aim of demonstrating the concept of umpolung in synthetic organic chemistry. Starting from a common alkyl sulfinate, students perform a polarity inversion by performing a Grignard-based sulfoxide synthesis and a Mannich-type formamide synthesis. The products are purified without chromatography and are easily characterized. Procedural optimization established an experiment time of less than 3 h. Spectroscopic characterization includes the interpretation of 1H NMR, 13C NMR, and FTIR spectra. This experiment, therefore, is suitable for a mid- to upper-level undergraduate organic lab curricula for illustrating advanced synthetic methods.