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and underwent thermal treatment to remove any residual carbamates. The ureas were then re-crystallized in pentane again and isolated via filtration to determine yield (Scheme 2a). 3.5. Synthesis of n-Propyl, Benzophenone(BP) Imine Propylamine (5 mmol) was added to 5 mL of dry methanol, followed by 2.5 mmol benzophenone Molecules 2016, 21, 24 8 of 11 (BP) and 3.3 mmol titanium(IV)-isopropoxide. The solution was stirred under nitrogen at room temperature while aliquots were taken at 3, 6 and 24 h for GC analysis and ATR-FTIR monitoring. Alternatively, the reaction was separated into 4 GC vials and sampled in-situ without stirring. Each GC Alternatively, the reaction was separated into 4 GC vials and sampled in-situ without stirring. Each vial represented a reaction vessel that was used to monitor the reaction kinetics (Scheme 2b). GC vial represented a reaction vessel that was used to monitor the reaction kinetics (Scheme 2b). Scheme 2. Reaction scheme showing the pathways for n-phenyl, n-alkyl urea synthesis in CHCl3 (a); Scheme 2. Reaction scheme showing the pathways for n-phenyl, n-alkyl urea synthesis in CHCl3 (a); and benzophenoneimine synthesis in methanol (b). and benzophenoneimine synthesis in methanol (b). 4. Conclusions 4. Conclusions In conclusion, we have shown that the reaction of CO2 with alkyl amines reduced the amine In conclusion, we have shown that the reaction of CO2 with alkyl amines reduced the amine reactivity resulting in reduced urea and imine yields for multiple primary amines. Performing the reactivity resulting in reduced urea and imine yields for multiple primary amines. Performing the reaction in the absence of a competing reaction demonstrates a true decrease in reactivity, rather than reaction in the absence of a competing reaction demonstrates a true decrease in reactivity, rather than preferentiality. Reversible carbamate formation via gaseous CO2 alone shows potential as a simple, “green” alternative compared to traditional methods that require harsh chemicals and more energy intensive reaction conditions; adhering to the major strategies of green chemistry which promote reduced solvent and energy use, inherently safer reagents, and reduced number of transformations. Despite the novelty, the temperature dependence of the reverse reaction does introduce limitations. The ability to efficiently protect and de-protect the amine and the solubility of the carbamates in the reaction media are also potential limitations. In future work, this protection mechanism will be implemented in a competitive reaction where amine functionality is required post protection for a separate coupling reaction. This will test the limits and efficiency of the proposed protection/de-protection technique. Also, this technique will be applied to high pressure systems in an attempt to dictate and shift the carbamate equilibrium to favor the protection. The energy input to maintain higher pressures may increase, but it is offset by the reduction in solvents for conducting the three separate steps in traditional protection methods. We anticipate that the results from this work will encourage chemists to not only design greener routes for amine protection/de-protection mechanisms, but also to learn about the many advantages that carbamate chemistry has to contribute to safer lab and industrial practices. Supplementary Materials: Supplementary materials can be accessed at: http://www.mdpi.com/1420-3049/ 21/1/24/s1. Acknowledgments: This work was funded by the American Chemical Society. Authors would like to acknowledge Paul Hernley for his experimental contributions to the study. Author Contributions: F.M. and C.K. conceived and designed the experiments; F.M. performed the experiments, analyzed the data and drafted the paper. C.K. oversaw the entire research study and coordinated the redaction of the manuscript. Conflicts of Interest: The authors declare no conflict of interest.PDF Image | Amines vs Nucleophilic Substitution Reversible Reaction CO2
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