10.1021/acs.joc.8b02074.s001 Taiki Yokoi Taiki Yokoi Hiroki Tanimoto Hiroki Tanimoto Tomomi Ueda Tomomi Ueda Tsumoru Morimoto Tsumoru Morimoto Kiyomi Kakiuchi Kiyomi Kakiuchi Site-Selective Conversion of Azido Groups at Carbonyl α‑Positions to Diazo Groups in Diazido and Triazido Compounds American Chemical Society 2018 site-selective conversions carbonyl α- position reaction conditions Diazo Groups site-selective conjugation paper reports α- diazo carbonyl groups alkyl azido groups β- elimination alkyl azides Site-Selective Conversion Azido Groups diazo compounds Triazido Compounds triazido molecule 2018-09-26 21:29:41 Journal contribution https://acs.figshare.com/articles/journal_contribution/Site-Selective_Conversion_of_Azido_Groups_at_Carbonyl_Positions_to_Diazo_Groups_in_Diazido_and_Triazido_Compounds/7138049 This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.