10.1021/ja3014105.s001 Jonathan P. Moerdyk Jonathan P. Moerdyk Christopher W. Bielawski Christopher W. Bielawski Alkyne and Reversible Nitrile Activation: <i>N</i>,<i>N</i>′-Diamidocarbene-Facilitated Synthesis of Cyclopropenes, Cyclopropenones, and Azirines American Chemical Society 2012 reaction conditions manner Subsequent hydrolysis acid variety isolable toluene Keq synthesis diamidocyclopropene Cyclopropenone combination Alkyne aryl nitriles cyclopropenone Cyclopropene AzirinesWe report alkyl DAC alkyne Reversible Nitrile Activation Synthesi cyclopropene 2012-04-11 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Alkyne_and_Reversible_Nitrile_Activation_i_N_i_i_N_i_Diamidocarbene_Facilitated_Synthesis_of_Cyclopropenes_Cyclopropenones_and_Azirines/2531926 We report the synthesis of a variety of diamidocyclopropenes by combining an isolable and readily accessible <i>N</i>,<i>N</i>′-diamidocarbene (DAC) with a range of alkynes (nine examples, 68–97% yield). Subsequent hydrolysis of selected cyclopropenes afforded the corresponding cyclopropenones or α,β-unsaturated acids, depending on the reaction conditions. In addition, the combination of a DAC with alkyl or aryl nitriles was found to form 2<i>H</i>-azirines in a reversible manner (four examples, <i>K</i><sub>eq</sub> = 4–72 M<sup>–1</sup> at 30 °C in toluene).