18.7. Addition of Phosphorus Ylides; The Wittig Reaction
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Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig ReactionEric Martin and Cynthia Kellen-Yuen A microwave-assisted Wittig reaction has been developed for the organic teaching laboratory. Utilizing this technique, a variety of styrene derivatives have been synthesized from aromatic aldehydes in good yields. The mixture of cis and trans alkenes produced also provides instructors with opportunities to emphasize the spectroscopic analysis of product mixtures. Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ.2007, 84, 2004.
Aldehydes / Ketones |
Alkenes |
Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Synthesis
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory ExperimentSam H. Leung and Stephen A. Angel In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry. Leung, Sam H.; Angel, Stephen A. J. Chem. Educ.2004, 81, 1492.
