3H-Azepines and related systems. Part 5. Photo-induced ring expansions of o-azidobenzonitriles to 3-cyano- and 7-cyano-3H-azepin-2(1H)-ones was written by Lamara, Kaddour;Redhouse, Alan D.;Smalley, Robert K.;Thompson, J. Robin. And the article was included in Tetrahedron in 1994.HPLC of Formula: 64113-86-6 This article mentions the following:
Unlike other aryl azides bearing electron-withdrawing ortho-substituents, o-azidobenzonitriles on photolysis in aqueous-tetrahydrofuran yield mixtures of the expected 3-cyano- (I; R=CN, R1 = R2 = H) and the unexpected 7-cyano-3H-azepin-2(1H)-ones (I; R = R1 = H, R2 = CN). In one instance ring-contraction to 2-azabicyclo[3.2.0]hept-6-en-3-one II is noted. X-Ray crystallog. data for 7-cyano- (I; R = R1 = H, R2 = CN) and 4-chloro-7-cyano-3H-azepin-2-one (R = H, R1 = Cl, R2 = CN) , and for the azabicycloheptenone, are presented. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6HPLC of Formula: 64113-86-6).
5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. The R-C-N bond angle in and nitrile is 180鎺?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 锜? bond in the triple bond. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).HPLC of Formula: 64113-86-6
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts