10.1021/ja045608c.s001 Joseph M. Mahoney Joseph M. Mahoney Colin R. Smith Colin R. Smith Jeffrey N. Johnston Jeffrey N. Johnston Brønsted Acid-Promoted Olefin Aziridination and Formal <i>a</i><i>nti</i>-Aminohydroxylation American Chemical Society 2005 Active ester substrates protonated aziridine triflic acid azide nucleophilic carbonyl triazoline need olefin aminohydroxylation aziridine production N 2 2005-02-09 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Br_nsted_Acid_Promoted_Olefin_Aziridination_and_Formal_i_a_i_i_nti_i_Aminohydroxylation/3301735 A straightforward synthesis of aziridines is reported from an electron-rich azide (alkyl or aryl azide), electron-deficient olefin, and triflic acid in cold acetonitrile. The only coproduct of the reaction is dinitrogen (N<sub>2</sub>). Active ester substrates bearing a nucleophilic carbonyl engage the putative protonated aziridine intermediate to produce the product of olefin aminohydroxylation in which the nitrogen is benzyl protected and the oxygen is acylated. The possibility that a triazoline need not be an intermediate in aziridine production is advanced.