World Journal of Chemical Education
ISSN (Print): 2375-1665 ISSN (Online): 2375-1657 Website: http://www.sciepub.com/journal/wjce Editor-in-chief: Prof. V. Jagannadham
Open Access
Journal Browser
Go
World Journal of Chemical Education. 2016, 4(5), 101-106
DOI: 10.12691/wjce-4-5-2
Open AccessArticle

A Highly Versatile One-Pot Aqueous Wittig Reaction

Forest J. Robertson1,

1Department of Chemistry, Western Connecticut State University, Danbury

Pub. Date: September 06, 2016

Cite this paper:
Forest J. Robertson. A Highly Versatile One-Pot Aqueous Wittig Reaction. World Journal of Chemical Education. 2016; 4(5):101-106. doi: 10.12691/wjce-4-5-2

Abstract

The implementation of green chemistry experiments in the sophomore organic teaching lab is essential in order to increase student awareness of issues that pertain to sustainability and reducing waste that impacts the environment. Aspects of green chemistry that draw attention to these important issues include, but are not limited to, the use of safer solvents, the development of energy efficient reactions, the use of less hazardous chemicals, and the prevention of waste. To demonstrate the ease of introducing green chemistry principles into the organic chemistry teaching lab a Wittig reaction was chosen to be “greened.” The green Wittig reaction described within this report was performed at ambient temperature and in an aqueous medium; in addition, the reaction was complete within one hour, and the transformation was accomplished in “one-pot.” Finally, students analyzed the Wittig products using 1H NMR spectroscopy to confirm structure and to determine the E:Z ratio.

Keywords:
second-year undergraduate organic chemistry inquiry-based problem solving Wittig reaction green chemistry

Creative CommonsThis work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

References:

[1]  Singh, M. M.; Szafran, Zvi; Pike, R. M. Microscale Chemistry and Green Chemistry: Complementary Pedagogies. J. Chem. Educ.1999, 76(12), 1684-1686.
 
[2]  Hjeresen, D. L.; Shutt, D. L.; Boese, J. M. Green Chemistry and Education. J. Chem. Educ.2000, 77(12), 1543-1547.
 
[3]  Kirchhoff, M. M. Topics in Green Chemistry. J. Chem. Educ.2001, 78(12), 1577.
 
[4]  Nguyen, K. C.; Weizman, H. Greening Wittig Reactions: Solvent-Free Synthesis of Ethyl trans-Cinnamate and trans-3-(9-Anthryl)-2-Propenoic Acid Ethyl Ester. J. Chem. Educ. 2007, 84(1), 119-121.
 
[5]  Haack, J. A.; Hutchison, J. E.; Kirchhoff, M. M.; Levy, I. J. Going Green: Lecture Assignments and Lab Experiences for the College Curriculum. J. Chem. Educ. 2005, 82 (7), 974.
 
[6]  Leung, S. H.; Angel, S. A. Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment. J. Chem. Educ. 2004, 81 (10), 1492-1493.
 
[7]  Reed, S. M.; Hutchison, J. E. Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid. J. Chem. Educ. 2000, 77 (12), 1627-1629.
 
[8]  Coulombel, L.; Weiwer, M.; Duñach, E. Aluminum TriflateCatalysed Cyclisation of Unsaturated Alcohols: Novel Synthesis of Rose Oxide and Analogues. Eur. J. Org. Chem. 2009, 33, 5788-5795.
 
[9]  Herrero, A. M.; Kremsner, J. M.; Kappe, O. C. Nonthermal microwave effects revisited: on the importance of internal temperature monitoring and agitation in microwave chemistry. J. Org. Chem. 2008, 73 (1), 36-47.
 
[10]  Skatova, A.; Fedushkin, I.; Maslova, O.; Hummert, M.; Schumann, H. Synthesis and structures of new conformationally rigid 1-aza-1,3-dienes of the acenaphthene series. Russ. Chem. B+2007, 56 (11), 2284-2289.
 
[11]  Shen, W.; Mao, J.; Sun, J.; Sun, M.; Zhang, C. Synthesis and biological evaluation of resveratrol-coumarin hybrid compounds as potential antitumor agents. Med. Chem. Res. 2013, 22 (4), 1630-1640.
 
[12]  Colabufo, N. A.; Berardi, F.; Perrone, R.; Rapposelli, S.; Digiacomo, M.; Balsamo, A. Arylmethyloxyphenyl Derivatives: Small Molecules Displaying P-Glycoprotein Inhibition. J. Med. Chem. 2006, 49 (22), 6607-6613.
 
[13]  Sun, Q.; Ma, S.; Dai, Z.; Meng, X.; Xiao, F-S. A hierarchical porous ionic organic polymer as a new platform for heterogeneous phase transfer catalysis. J. Mater. Chem. A 2015, 3, 23871-23875.
 
[14]  Nashy, E-S. H. A.; Megahed, M. G.; El-Ghaffar, M. A. A. Preparation of Fat-Liquor Based on Jojoba Oil Under Phase Transfer Catalysis. J. Am. Oil Chem. Soc. 2011, 88(8), 1239-1246.
 
[15]  Speed, T. J.; McIntyre, J. P; Thamattoor, D. M. Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate. J. Chem. Educ. 2004, 81(9), 1355-1356.
 
[16]  Ramakrishna, N. V. S.; Jain, A. K.; Ghate, A. V.; Gupte, R. D.; Vadlamudi, R. V. S. V. Synthesis and Na+/H+ exchange inhibitory activity of indanylideneacetylguanidines. Indian J. Chem. B 1999, 38 (4), 407-412.
 
[17]  Andrews, I. P.; Kwon, O. Phosphine-Catalyzed [3+2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-Phenyl-1-Tosyl-3-Pyrroline-3-Carboxylate. Org. Synth. 2011, 88, 138-151.
 
[18]  Kelly, M. J. B.; Fallot, L. B.; Gustafson, J. L.; Bergdahl, B. M. Water Mediated Wittig Reactions of Aldehydes in the Teaching Laboratory: Using Sodium Bicarbonate for the in Situ Formation ofStabilized Ylides. J. Chem. Educ. 2016.
 
[19]  El-Batta, A.; Jiang, C.; Zhao, W.; Anness, R.; Cooksy, A. L.; Bergdahl, M. Wittig Reactions in Water Media Employing Stabilized Ylides with Aldehydes. Synthesis of, -Unsaturated Esters from Mixing Aldehydes, α-Bromoesters, and Ph3P in Aqueous NaHCO3. J. Org. Chem. 2007, 72 (14), 5244-5259.
 
[20]  Wu, J.; Yue, C. One-Pot Wittig Reactions in Aqueous Media: A Rapid and Environmentally Benign Synthesis of α, β-Unsaturated Carboxylic Esters and Nitriles. Synthetic Commun. 2006, 36 (20), 2939-2947.