28951-73-7Relevant academic research and scientific papers
A nitrile-stabilized ammonium ylide as a masked C-C=N synthon in heterocyclization with amidine-imine: 3-component assembly to fused pyrimidine scaffolds
Guchhait, Sankar K.,Saini, Meenu,Sumkaria, Divyani,Chaudhary, Vikas
, p. 6941 - 6944 (2017)
A unique reactivity of a nitrile-stabilized quaternary ammonium ylide as a masked C-CN synthon in contrast to its usual sigmatropic rearrangement has been demonstrated. Its reaction with 2-aminopyridine-derived aldimine undergoes electronically-assisted n
Propylphosphonic anhydride (T3P) catalyzed one-pot synthesis of α-aminonitriles
Reddy, Sirigireddy Sudharsan,Reddy, Bhoomireddy Rajendra Prasad,Reddy, Peddiahgari Vasu Govardhana
, p. 739 - 743 (2015/08/03)
Abstract The Strecker reaction was performed via a one-pot three component condensation of hetero aromatic/aromatic aldehydes, secondary amines and trimetylsilyl cyanide in the presence of propylphosphonic anhydride (T3P) to accomplish the corresponding α-aminonitriles. The main advantages of this method are very short reaction time and excellent yields.
Steric Inhibition of Synergistic Radical Stabilizing Effects
Bordwell, F. G.,Bausch, Mark J.,Cheng, Jin-Pei,Cripe, Thomas H.,Lynch, Tsuei-Yun,Mueller, Mark E.
, p. 58 - 63 (2007/10/02)
Equilibrium acidities in Me2SO for 14 α-N-morpholinyl-, 6 α-N-piperidinyl-, and 7 α-cyclohexylarylacetonitriles and the oxidation potentials of their conjugate bases have been determined.The increased pKHA values by about 2 units observed in these systems, relative to the corresponding arylacetonitriles, is ascribed to the presence of increased steric constraints in the anions.Hammett plots revealed larger ρ values than for arylacetonitriles (6-7 versus 5.5), pointing to an increased negative charge density on the benzylic carbon atoms in the anions.A plot of anion oxidation potentials, Eox(A-), versus pKHA for the α-N-morpholinylarylacetonitriles was linear with a slope near unity, showing that remote substituents for the most part have very little effect on radical stabilities.A 5 and 6 kcal/mol lowering of the BDE of the acidic C-H bond caused by replacing the cyclohexyl group in α-cyclohexylphenylacetonitrile by α-N-morpholinyl or N-piperidinyl groups, respectively, is attributed to the strong donor properties of these amino functions.The effects are only about one-third as large, however, as similar effects in R2NCH2COPh, where the steric effect of Ph is absent and a synergistic effect is believed to be operative.
