A Feasible Approach to Cubane Synthesis and Functionalization
Session Number
Project ID: CHEM 06
Advisor(s)
Dr. Laura Kopff, Illinois Mathematics and Science Academy
Discipline
Chemistry
Start Date
17-4-2024 8:35 AM
End Date
17-4-2024 8:50 AM
Abstract
In the 60 years since cubane’s synthesis, the hydrocarbon cube has displayed considerable practicality within medicinal chemistry as a bioisostere to benzene. However, modern synthesis procedures of cubane call for known carcinogenic compounds, namely benzene, which can be a limitation for laboratories looking to synthesize cubane for research. In this study, researchers looked at a synthesis of cubane that substitutes a less toxic reagent, toluene, for benzene. Furthermore, functionalization of cubane using standard aromatic reactions was attempted in order to look at the efficiency of adding substituents to the compound. Prior to functionalization, the product obtained from the synthesis was analyzed using IR, NMR, and TLC and compared against the literature to confirm the presence of cubane. All derivatives of the cubane compound were similarly analyzed using NMR and IR spectroscopy to confirm structure. The researchers of this study hope that the synthesis used allows accessibility to more laboratories looking to synthesize cubane, and the results from functionalization attempts contribute to a basis for further research in cubane derivatives.
A Feasible Approach to Cubane Synthesis and Functionalization
In the 60 years since cubane’s synthesis, the hydrocarbon cube has displayed considerable practicality within medicinal chemistry as a bioisostere to benzene. However, modern synthesis procedures of cubane call for known carcinogenic compounds, namely benzene, which can be a limitation for laboratories looking to synthesize cubane for research. In this study, researchers looked at a synthesis of cubane that substitutes a less toxic reagent, toluene, for benzene. Furthermore, functionalization of cubane using standard aromatic reactions was attempted in order to look at the efficiency of adding substituents to the compound. Prior to functionalization, the product obtained from the synthesis was analyzed using IR, NMR, and TLC and compared against the literature to confirm the presence of cubane. All derivatives of the cubane compound were similarly analyzed using NMR and IR spectroscopy to confirm structure. The researchers of this study hope that the synthesis used allows accessibility to more laboratories looking to synthesize cubane, and the results from functionalization attempts contribute to a basis for further research in cubane derivatives.