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ERIC Number: EJ1110413
Record Type: Journal
Publication Date: 2016-Aug
Pages: 5
Abstractor: As Provided
ISSN: ISSN-0021-9584
The Two Faces of Sulfinates: Illustrating Umpolung Reactivity
Tapia-Pineda, Adabelia; Perez-Arrieta, Carlos; Silva-Cuevas, Carolina; Paleo, Ehecatl; Lujan-Montelongo, J. Armando
Journal of Chemical Education, v93 n8 p1470-1474 Aug 2016
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 [superscript 1]H NMR, [superscript 13]C NMR, and FTIR spectra. This experiment, therefore, is suitable for a mid- to upper-level undergraduate organic lab curricula for illustrating advanced synthetic methods.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A