10.1021/acs.orglett.9b01430.s001 Prasenjit Sau Prasenjit Sau Amitava Rakshit Amitava Rakshit Tipu Alam Tipu Alam Hemant Kumar Srivastava Hemant Kumar Srivastava Bhisma K. Patel Bhisma K. Patel <i>tert</i>-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4<i>H</i>)‑ones from Terminal Aryl Alkenes American Chemical Society 2019 one biradical reaction N atoms Terminal Aryl Alkenes tert terminal aryl alkenes carbonyl oxygen Butyl nitrite 3- TBN Butyl Nitrite Mediated Synthesis bond 2019-06-17 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/_i_tert_i_-Butyl_Nitrite_Mediated_Synthesis_of_1_2_4-Oxadiazol-5_4_i_H_i_ones_from_Terminal_Aryl_Alkenes/8285780 <i>tert</i>-Butyl nitrite (TBN) mediated synthesis of 3-aryl-1,2,4-oxadiazol-5­(4<i>H</i>)-ones has been accomplished using terminal aryl alkenes via a biradical reaction intermediate. Three consecutive sp<sup>2</sup> C–H bond functionalizations of styrenes afforded 3-phenyl-1,2,4-oxadiazol-5­(4<i>H</i>)-ones via the formation of new CN, CO, C–O, and two C–N bonds. Both of the N atoms originate from TBN, while the carbonyl oxygen is from the water (moisture) the other oxygen from the NO part of the TBN.