Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a beta-Bromostyrene

• Thomas A. Evans ^[1]
  1. [1] Denison University

     Denison University

     Township of Granville, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 83, Nº 7, 2006, pág. 1062
• Idioma: inglés
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• Resumen

  • The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. The product is purified by dry column vacuum chromatography and its stereochemistry is determined by 1H NMR. TLC, GC and GC–MSD can also be used. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes.