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The Synthesis of Oxazolidinones from Aziridines and Carbon Dioxide

Phung, Chau V

Abstract Details

2016, PhD, University of Cincinnati, Arts and Sciences: Chemistry.
It has been discovered that ammonium iodide acts as an efficient catalyst to convert an N-alkylaziridine to an oxazolidinone(s). The catalytic ability of NH4I comes from the synergic effect of the hydrogen bonding and the nucleophilic halide. The reaction proceeds in high yield, excellent chemo- and regioselectivity. The selectivity of the product can be tuned by changing pressure and temperature. 1-Benzyl-2-methylaziridine behaves inconsistently in the reaction with carbon dioxide without any additive. It has been found that this aziridine, or generally, any 1,2-dialkylaziridine is not reactive at rt based on a combination of experimental and computational studies. In cases where there was a reaction, an impurity in the starting material acted as a catalyst. This impurity is very difficult to remove from the starting material using column chromatography. The amount was diminutive that it did not show up spectroscopically. When the newly found catalyst is involved, the reaction with carbon dioxide is 0th order with respect to aziridine. This catalyst is also accountable for the dimerization of the aziridine on the bench. The mechanisms for the reaction with carbon dioxide and the dimerization are thus proposed.
Allan Pinhas, Ph.D. (Committee Chair)
Bruce Ault, Ph.D. (Committee Member)
David Smithrud, Ph.D. (Committee Member)
152 p.

Recommended Citations

Citations

  • Phung, C. V. (2016). The Synthesis of Oxazolidinones from Aziridines and Carbon Dioxide [Doctoral dissertation, University of Cincinnati]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1470741529

    APA Style (7th edition)

  • Phung, Chau. The Synthesis of Oxazolidinones from Aziridines and Carbon Dioxide. 2016. University of Cincinnati, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ucin1470741529.

    MLA Style (8th edition)

  • Phung, Chau. "The Synthesis of Oxazolidinones from Aziridines and Carbon Dioxide." Doctoral dissertation, University of Cincinnati, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1470741529

    Chicago Manual of Style (17th edition)