Spectrographic method for the detection of active methylene groups and synthesis of several styrene and stilbene derivatives. VI. Amino derivatives of phenylacetonitrile was written by Boyer, Jacqueline;Bruylants, Albert. And the article was included in Bulletin de la Societe Chimique de France in 1958.Product Details of 67197-53-9 This article mentions the following:
The reactivity of m- and p-amino derivatives of PhCH2CN in condensations with BzH and its p-NMe2 derivative decreases with decreasing acidity of the CH2CN group. The order of acidity produced by the following substituents in PhCH2CN, as determined by comparison of spectra in EtOH and EtONa, is: H ∼ p-Me3NI ∼ m-Me3NI ≫ p-NH2 > m-NH2 > p-Me2N ≫ m-Me2N. Changes in spectra with time in EtONa show that the ionization of the last four of these is slow. The m- and p-NH2 derivatives react with BzH and p-Me2NC6H4CHO to yield principally the azomethines, but the other compounds give high yields of α-cyanostilbenes after 40 hrs. in alc. EtONa. The following cyanostilbenes, XC6H4C(CN):CHC6H4Y, were obtained (X, Y, yield, and m.p. are given): p-Me3NI, H, 85, 175-98° (geometric isomers); p-Me3NI, p-NMe2, 87, 195-6.5°; p-Me2N, H, 87, 136-7°; p-Me2N, p-NMe2, 85, 196-7.5°; m-Me3NI, H, 88, 172-97° (geometric isomers); m-Me3NI, p-NMe2, 92, 161-2°; m-Me2N, H, 90, -; m-Me2N, p-NMe2, 88, 117-208°. The p-H2NC6H4CH2CN and its m-isomer, b8 179-80° (HCl salt, m. 199-201°), were prepared by reduction of the corresponding nitro compounds with SnCl2, quaternized with MeI to the p-Me3NI, m. 167-8°, and m-Me3NI, m. 173-4°, derivatives resp., and these were demethylated to p-Me2NC6H4CH2CN, m. 53.5-55°, and its m-isomer, m. 173-4°, resp. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Product Details of 67197-53-9).
2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Product Details of 67197-53-9
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts