Moerdyk, Jonathan P. Bielawski, Christopher W. Alkyne and Reversible Nitrile Activation: <i>N</i>,<i>N</i>′-Diamidocarbene-Facilitated Synthesis of Cyclopropenes, Cyclopropenones, and Azirines 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). 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
    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
10.1021/ja3014105.s001