Wittig Reaction: The Synthesis of trans-9-(2-Phenylethenyl)anthracene Revisited

Jaworek, Christine; Iacobucci, Sarah

doi:10.1021/ed079p111

Cited by 8 publications

(8 citation statements)

References 4 publications

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“…The flask was loosely stoppered, placed in an ice bath, and stirred for at least 10 minutes. After this time, (carbethoxymethylene)triphenylphosphorane 2 (2.0 g, 5.7 mmol) was slowly added to the flask. Stirring was continued in the ice bath for an additional ten minutes after which time the solution was allowed to warm up to room temperature.…”

Section: Methodsmentioning

confidence: 99%

Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate

2004

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The synthesis of ethyl trans-cinnamate, by the reaction of benzaldehyde with the stabilized phosphorus ylid (carbethoxymethylene)triphenylphosphorane, serves as a useful experiment to illustrate the Wittig reaction in the introductory organic chemistry laboratory. The reaction is highly stereoselective and affords the product in excellent yield and purity. The stereochemistry of the product is established by examining the coupling constants displayed by the olefinic protons in the 1H NMR spectrum. The experiment highlights several important aspects of organic chemistry such as synthesis, stereochemistry, instrumental analysis, and molecular modeling.

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Section: Methodsmentioning

confidence: 99%

Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate

2004

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“…The resulting alkene was isolated via several extractions using diethyl ether, followed by column chromatography . Modifications have been published that show that a milder base can be used with benzyltriphenylphosphonium chloride to form the ylide, N , N -dimethylformamide (DMF) can replace diethyl ether or methylene chloride as the reaction solvent, and the extraction can be replaced by precipitating the alkene from the reaction mixture …”

Section: The Wittig Reactionmentioning

confidence: 99%

“…The Wittig reaction has been an important reaction for exact placement of an alkene within a molecule since it was first published in 1954 . It has been well represented with examples in the undergraduate organic laboratory curriculum. − Examples include using stabilized ylides, − hand milling in a solvent-free environment, alumina support without solvent, and others accomplished via microwave-assisted reactions. , There has been much interest in aqueous examples of the Wittig reaction; ,− therefore, a broadly applicable version was sought that could be completed successfully during a three-hour organic chemistry lab period. The approach was planned to teach principles of green chemistry, reduce hazardous waste, and teach structure determination by integrating it into a case study-based learning module.…”

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confidence: 99%

Green Aqueous Wittig Reaction: Teaching Green Chemistry in Organic Teaching Laboratories

et al. 2014

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Green experiments in the organic teaching lab are a vital part of training a new generation of scientists. Not only do they make the lab experience safer and produce less costly waste, they allow students an opportunity to examine and consider potentially hazardous chemical methodologies and develop alternatives. The work discussed here focuses on a series of Wittig reactions that are carried out in aqueous conditions, at room temperature, and in less than one hour. The reactions have been applied to a variety of starting aldehydes. Results for this work and strategies for implementing a green chemistry case study into the laboratory curriculum are presented.

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“…This laboratory experiment focuses on the synthesis of compounds which produce fluorescence and chemiluminescence through the production of a biphasic fluorescent and chemiluminescent glow stick. Although there are several laboratories and demonstrations which take advantage of fluorescence and chemiluminescence separately as well as the synthesis of dyes and fluorophores, , this experiment combines multiple synthetic organic reactions to fabricate a biphasic glow stick, in addition to in-depth exploration of fluorescence and chemiluminescence. The synthesis of bis(2,4,6-trichlorophenyl) oxalate (TCPO; used for energy generation in glow sticks to produce chemiluminescence) in a teaching laboratory setting is novel and teaches basic laboratory techniques used in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

General Chemistry Laboratory Experiment To Demonstrate Organic Synthesis, Fluorescence, and Chemiluminescence through Production of a Biphasic Glow Stick

2017

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A laboratory experiment is described for beginning, nonmajor chemistry students, which allows students to examine the phenomena of fluorescence and chemiluminescence, as well as gain experience in basic organic synthesis. Students synthesize fluorescein and bis(2,4,6-trichlorophenyl) oxalate (TCPO) to explore fluorescence and chemiluminescence by assembling a biphasic glow stick. The experiment gives students the opportunity to understand the chemistry behind common “real-life” experiences of glow stick illumination and fluorescent lighting or inks and to synthesize compounds that exhibit these phenomena. Students’ survey data between 2013 and 2016 show that the experiment was enjoyable to undergraduate nonscience majors (4.3 of 5 cumulative, 4.8 in 2016) and relevant to their lives (4.0 of 5 cumulative, 4.4 in 2016).

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Wittig Reaction: The Synthesis of trans-9-(2-Phenylethenyl)anthracene Revisited

Cited by 8 publications

References 4 publications

Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate

Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate

Green Aqueous Wittig Reaction: Teaching Green Chemistry in Organic Teaching Laboratories

General Chemistry Laboratory Experiment To Demonstrate Organic Synthesis, Fluorescence, and Chemiluminescence through Production of a Biphasic Glow Stick

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