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The rhodium(II)-catalyzed intramolecular aziridination of an aromatic carbamate is reported. The resulting aziridine can be selectively opened via nucleophilic addition to form either benzoxazinone or benzoxazipine bicylic scaffolds. The aziridination reaction was performed under microwave irradiation in the presence of catalytic Rh2(OAc)4, PhI(OAc)2, and MgO. The methodology could provide an efficient stereoselective means of introducing nitrogen functionality into relatively complex molecules. The results are still under investigation.
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Steinauer, Nathaniel Stephen, "RHODIUM(II)-CATALYZED INTRAMOLECULAR AZIRIDINATION TO FORM BENZOXAZINONE AND BENZOXAZIPINE DERIVATIVES" (2013). Senior Projects Spring 2013. 37.