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).