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[2+2] dimerization of cinnamylidenemalonic acid

WCU Author/Contributor (non-WCU co-authors, if there are any, appear on document)
Shana Weathersby (Creator)
Institution
Western Carolina University (WCU )
Web Site: http://www.wcu.edu/404.asp
Advisor
Brian Dinkelmeyer

Abstract: The original goal of the proposed research project was to crystallize a chiral host molecule with a diene-containing quest molecule to produce stereoselective molecules in a solid state reaction. These topochemical reactions occur within a crystalline matrix and impart the stereochemistry of the starting material to the product. Tartaric acid was used as a host because it was inexpensive and had a consistent mode of molecular packing and Muconic acid derivatives were synthesized and used as guest molecules. However, solubility problems prevented any co crystal reactions from taking place. Crystal structures were obtained for the host compounds. The focus of the rest of the project was then turned to a potential guest compound, cinnamylidenemalonic acid. Cinnamylidenemalonic acid was found to crystallize in three different polymorphic structures each of which underwent photochemical reaction when irradiated with 257.3A of light. Products of photochemical reactions were characterized by proton NMR. Polymorph 1 gave a mixture of products, while polymorphs 2 and 3 formed the same [2+2] dimerization product. Infrared spectroscopy and proton NMR were used to study the solid state photochemistry of the compound in an attempt to find a suitable rate law.

Additional Information

Publication
Thesis
Language: English
Date: 2010
Subjects
Crystallography -- Industrial applications
Polymerization